(oN hed Chemical Components of Cells AL Gst sight, 1s dieu to comprehend tht ving creatures are merely ‘chemical systems. Their incredible diversity of form, thet seemingly pu [pose benaiior,and thei ably to grow and reprocuce all seam fo set them apart trom the world ofsoids, liquid, and gases Uhl chemisty nor mally describes, Indeed, unt the late nineteenth century, it was widely believed that al ving things contained a vital force an “animusthat was tesponsble for thelr distinctive properties. ‘we now know that there fs nothing in a Hving organism that dsobeys chemical or physical laws. However, the chemistry of ife Is indeed 3 Special kin ist ts based overwhelmingly on carbon compounds, the sludy of whichis known as organic chemist. Second, it depends almost ‘exclusively on chemical reactions tha take lace ina watery, or aqueous, ‘environment and in Hie relatively narow range of temperatures exper ‘enced on Earth. Third tis enormously complex: even the simplest cell's ‘yasly nvore complicted ine chemistry than any other chemical sytem known. Fourth, iis dominated and coordinated by collections of large polymers—molecules made of many chemical subunits linked end-o- ‘end whose unique properties enable cells and organisms to grow and reproduce and 10 do all the other things that are characenstic of lie Finally the chemistry of lei tightly regulated: cells deploy a wide van- dy of mechanisms to make sure that each of ther chemical reactions ‘curs al the proper rat, time, and pace Because chemistry lies al the heal of lbiology, inthis chapler, we biel survey the chemistry ofthe ving el. We will meet the molecules from which cols are made and cxamine thor structures, shapes, and chemical ‘properties, These molecules determine the size tructue, and functions ‘CHEMICAL BONDS: SMALL MOLECULES IN CELLS MACROMOLECULES IN CELLS‘Bataleon wl bound thr. “pe amar the wren oud anges rom abet ten fr ycosen) {Bapeu G4 nn for ama of gh atom ‘unbon,thanucourle vay much amar how's 10 rmtorcrton tr exp Iii acta wom toi, ‘nudes nous natbe esbe Co ASTER 2 Chemical Components of Cas fing cel. By understanding how they interact, we can begin to se= how cels expo the laws of chemisty and physics io survive, thrive, and reproduce. CHEMICAL BONDS Matter is made f combinations of cloments—substances such as hyro- [Ben or carbon that cannct be broken dau orinteconvertd by chemical ‘nears The smallest particle ofan element that stil etins its distinctive chemical properties isan ator. The characteristics of substances other than pure clements—including the materials fom which living cells are smade—depend on which atoms they contain and the way that these ‘toms are linked together in groups to form malocules. To understand living organisms, therefor, tis crucal to know bow the chemical Bonds that hold atoms logether in molecules ae formed, Cells Are Made of Relatively Few Types of Atoms Each atom has at its center a dense, positively charged nucleus, which | sutounded at some distance by a cloud of negatively charged electrons, held in orbit by electrostatic attraction tothe nucleus (Figure 22), The nucleus consists of two kinds of subatomic particles protons, which are positively charged, and neutrons, which are electrically neural. ‘The atomic numberof an clement fs determined bythe number of protons resent In ie atoms nucleus An stom of hytrogen has = nucles com= posed of single proton; so hydrogen, with an atomic number of, isthe lightest clement An alom of carbon has six protons in ts nucleus and an salomic number of Figure 2-2). ‘The electric charge cartied by each proton is exactly equal and opposite {othe charge carted by a single electron. Because the whole atom s elec Inicaly neutral, the number of negatively charged elecrons surrounding the nucleus is therefore equal to the number of postively charged pro= tons thatthe nucleus contains, thus the number Of electrons in an stom ‘also equals the omic number. All atoms of given element have the Same atomic number, and we will see shortly tha is his number that ‘igure 210 Carhor-catbon double ‘bonds ao shortor ad more gid han ‘arbon-crbon single bonds Ihe (Shane mall lasing covert Sonabeincer Bite ctbon atoms shone ‘he tevshecalarangerent ofthe thse ‘Sige covaent bones between 929 cbon ‘Fumand te veo utachod atone Tho re goups emedtyscoratrtc-C ‘ene croft aate fe one sneer round tabard mr Tow co ‘ondbetnees tee catsen atom in 2 oleae of etre hyena ates he. [Sori gocmatn ofthe eaten sere ak Ding athe toneto th same pare the sabe tone eevens the tation ot Soe Cig ecw othe shor eve Wy O=0 © @ ‘iguo 2:1 i pla covalent bond, ‘the eaciron shored une. ‘Sinan of sorter catitonsin the pal caaent bona sme of wtor (icnana te nenplar covalent bards ns ‘olecds of nygen (Os) MFO, deerore lomoresvongy atrscted tha oxygen cous ante the mucus, ainaested bythe outns ofthe parca negate hand patel poate Schenges 4sQUESTION 2-3 Dizeuss whathar tho fllowing cetera ‘bond cn. in princi, be thought of as avery polar covalent bond. Polar covalent bonds, then fol ‘somenners between onic bone eae ‘onpolr covalent bonds atthe ‘ther ond” Figure 2-12 sodium choi shld together by inl bonde 30m (faedion tay rescs wit anor oF {lone (Sb. lecronsct each ya mnths ect aly crore Fhe chamesly sco (reuse ‘Hl outermost shes te shown red “The eat as plac ih ano of 2 ole doctor fom sod to dota, {emg seca chagedstons or fom ech wih complete of lero Fri ouemen sole The wo lone hovo ppoata charge ad we held ogee by Sioatane santana proach ‘horeacon batoan sod ara cto, CCHAPTER2 Chemical Components of Cas To gel an idea of what bond strengths mean, iti helpful to compare them withthe sverage energies ofthe impacts that molecules continally| undergo onsing to collisions with other molecules in their environment thei thermal, O heat, energy Typical covalent bonds are strenger than these thermal energics hy a factor of 10, 59 they are cesistant fo Being pulled apart by thermal motions. In living organisms, covalent bands are ‘ormally broken only curing specie chemical reactions that ae careful ‘ontroles by highly specalred protein catalysts called ensymes lonic Bonds Form by the Gain and Loss of Electrons In some substances, the participating atoms are so diferent in eletro- ‘negativity that thei electrons are not shared at all—they ae transfered Completely to the more electronegative partner The resulting bonds, called ionic bonds, are usually formed betwen atoms that can attain ‘ completely filed outer shell most easily by donating electrons to—or ‘accepting electrons ftom—another atom, rather than by sharing them. For example, returning to Figure 2-8, we see that a sodium (Na) atom can achieve a flled outer shelby giving up the single electron ints third shel. By contras, a chlorine (Ch atom can compete its outer shell by gaining just one electron. Consequently fa Na atom encounters a Cl ‘atom, an electron can jump from the Na tothe Cl, leaving both atoms ‘with fled outer shells. The offspring ofthis marrage between sodium, 2 ‘ofl and inlensely eaclve meal, and chlorine, a toxic green gas, lable sak vac. When an electron jumps from Na to Cl, both atoms become electr- cally charged ions. The Na alom that lost an electron now has one less Cleclron than it has protons in ils nucleus; i therefore has net single postive charge Wa") The Cl atom that gained an electron now has one ‘more electron than thas protons and has a net single negative charge (Ch, Because oftheir opposte charges, the Ra" and Cr-fons are attracted to each other and are thereby held together by an tonic bond (Figure 2-124). ons held together solely by tonic bonds are generally called sats rather than molecules. A NaCl crystal contains astronomical numbers of ‘Na* and CI ons packed together In a precise, three-dimensional aay ‘wth thetr opposite charges exactly balanced: crystal only 1 mm across Contains about 2 10)? of each type Figure 2-128 and C). OO o© seewacne) —cumesene) ley auliMioy, w aeBecause ofthe favorable interaction betcen ions and water molecules (ehh ae polar, many sali (ncluding Nach are highly soluble in water ‘They dissociate inlo individual ions (such as Na" and Cl), each sur- rounded by a group of water molecules. Posvelons are called caons ‘and negative fons ae called anions. Small morganic ons suchas Na’, CT, and C22 play important parts in many biological processes, including the electrical acy of neve cells, as we disuse in Chapter |2. In aqueous solution, lonke bonds ate 10-100 times weaker than the cova lent bonds that hold atoms together in molecules. Hut, as we wil Se, ‘soch weak interactions nevertheles play an important roe nthe chen ‘sty efliving things. Hydrogen Bonds Are Important Noncovalent Bonds for Many Biological Molecules Water accounts for about 70% of cells weight, and most intracellular teactions sccurin an aquesusenvironment. Thus the propertcs of water hhave pul 2 permanent stamp on the chemistry of living things. In each ‘molecule of waler @0), the two covalent H-O bonds are highly polar because the O's strongly alaclive for electrons whereas the His only ‘weakly aliracve. Conseguenly in each water molecule, thee isa pre ponderance of positive charge on the (wo H atoms and negalve charge ‘onthe O. When a postvely charged region of one water molecule hat 5, one of H atom) comes close to 3 negatively charged region that 's, the 0) of a second water molecule, the elecirkal atvaction between them can establish a weak bond called a hydrogen bond (Figure 2-13) “These bonds are much weaker than covalent bonds and ae easly broken by random thermal motions. Thus each bond lasts only an exceedingly short Une. But the combined elfet of many weak bonds is far fom Uwvial. Each water molecule can form hydrogen bonds throug ts 40 H atoms to two other water molecules, producing a network in which Inydrogen bonds are being continually broken and formed ee Panel 2-3, 1p. 70-71. tis because of hase ntarlocking hydrogen bonds that water [Shscom tempersture iss ligud—ith a high boiling pont and high sur face tension and not 8 gas Without hydrogen bonds fe as we Enow ‘could mot exis Hydrogen bonds are not limited to water. n general, a hydrogen bond ‘can form whenever» postvely charged Hatem held in one molecsle ‘bya polar covalent nkage comes close to a negatively charged atom — typically an agen ora mtrogen—helonging ta another molecule (igure 225138), Hydrogen bonds can ako occur between diferent parts of 3 Single lange molecule, where they often help the molecule fd into 3 particular shape. Like molecules (or salts) that cary positive or negative charges, sub- ‘stances that contain polar bonds and can form hysrogen bonds also mix ‘ell with water. Such substances are termed hydrophilic, meaning that they are Water loving.”& large proportion ofthe molecules in the ague (ous environment ofa cel fall into this category, including sugars, DNA, RNA, and 3 majonty of proteins. Hydrophobic water fearing") mol ‘cles by contrast, are uncharged and form few or na hyagen Bonds ‘and they do net aisave i water. These and ether properties of water ‘ae reviewed in Panel 2-2 (pp. 68-69), Four Types of Weak Interactions Help Bring Molecules Together in Cells, ‘Much of biology depends on speciic but transient interactions between fone molecule and another. ‘These associations are mediated by Chemical Bonds 7 OHO OH NH iM ‘NH UML re 2-19 Noneovalnthyerogen bonds {lov bowwewn netrmcleaee a ‘betwesn many other pols moles, (ainbpogercend fe semen erin. fh sree cage ‘Stoccaly sracedto heap nogathe rage tte ongen stm nels, hyd bane canna aban ‘oletor acon an one Tereenteaae moe ‘Sem at Pirate the chao ee bonaseseste QUESTION 2 “rus orfilsa? “When Nociis soled water tho water toloculos clover to tho fonsFigure 2-14 large molec, sch 5 prota, can bind to ancthe prota ‘Sibel olech wolocda nite aqout ‘Enwronmen of aca maty nc weak Piscine oad onset tre sete ‘recognae each shes spectaly and Term stgu compan Show hates 42 chUDTER2 creme Components ot cats roncovalent bonds suchasthe hydrogen hondsjust discussed. Alhough {hese noncovalent bond are incvidusly quite weak, tir energies an sum to create anellecive force between two molecules, ‘The ionic bonds that hold together the Na* and Cl-ions in a salt crystal (see Figure 2-12) represent 2 second form of noncovalent bond ealled an lectrostaic attraction. Ledtrastatic attractions ate sirngest when the atoms involved are fully charged, as are Na’ and Cl ions. Bul a weaker lecrostatcalraction can occur between molecules tht conan polat ‘covalent bonds (see Figure 2-11). Uke hydrogen bonds, electosalle tations are extremely important in blology For example, any lange molecule with many polar groups wil have pattem of partial positive {ind negative charges on ft surface. When auch 2 molectle enceunters 4 second molecule with 3 complementary st of charges, the two wall bbe drawn fo each other ty eleeoststic traction Even though water greatly reduces the strength ofthese allrctions in mest biological set- UUngs, the large mumber of weak noncovalent bonds that form oa the suriaces of large molecules can nevertheless promote trong and speci Dinding Figure 2-14), ‘A thi type of noncovalent bond, calls! a van dee Waals attraction, ‘comes ino play when any wo aloms approach each other closely. These honspecic Inieractons spring from fctuations In the distribution of elects in every atom, which can generat a transient traction when {he atoms are in ery close proximly. These weak atractions oxcur in ll ‘ypes of molecules, even those tht are nonpolar and cannot form ionic ‘or hydrogen bonds. The relative lengths and strenglhs of these thee ‘ypes of noncavaion bonds sre compared tothe longth and strength of | covalent nds In Table 2-1 ‘ThefourthefTect that often brings moleculestogether knot, strictly speak: ing, a bond at al in an aqueous enviroment, a hydrophobic force is {generated by a pushing of nonpolar surfaces out ofthe hydrogen-bonded ‘water network, where they Would ctherwise pysicaly Intrfere with the Tigh Tavorabie interactions between water molectles. Hydrophobic Jnrcos play an important part tm promoting molecular interactions in panicular, in building cel membranes, which are constructed largely ‘rom lipid molecues with long hydrocarbon talls.in these molecules, the atoms are covalently linked to C atoms by nanpolar bands sce Panel 251 ppc), Hecause the stomshave almost no et postive charge, ‘hey cannot fms efactive hjdogen bonds foster molecules, inchalng water. AS 2 result lips ean form the thin membrane bares that keep the aqueous interior of the cell separate from the surrounding aqucous ‘environment, AL our types of weak chemical interactions important in blelogy are ‘reviewed in Panel 2-3 (pp. 70-71), are See) covert ee a os asi) 12601 Neneovalnt hyogentond O17 vara a2t Nancoalrvan dor Wa os exon cana, Siracion atom ee ee EER cms emer‘Some Polar Molecules Form Acids and Bases in Water ‘One of the simplest kinds of chemical reaction, and one that has pro- ound signifcance for cells, takes place when a molecule with 3 highly polar covalent bond between a hydrogen and another atom dissolves in ‘water, The hydrogen atom in such a bond has given ups elecron almost enlirely tothe companion atom, soit =xstsas an almost naked positively charged hydrogen nucleus—in other words, proton (When the polat ‘molecule becomes surrounded by water molecules, the proton wil be altace tothe partial negative charge on the oxygen atom of an adie ent water molecule (see Figure 2-11}; this proton can thus dissocial= from is original partner and associate instead withthe oxygen alom of the water molecule, generating 2 hydronium fon (H40°) Figure 2-152), “The reverse reaction—in which a hydronium ion releases a {kes place very readily, son an aqueeus solution, billons of protons are constantly iting to and iro between ane molecule and another ‘substances that release protons when they lssolve in water, thus form Ing Ha0>, are termed acids. The higher the concentration of #30", the ‘more acc the solution. Even in pure Water, Hs0* is presen ata concen- Walon of 10", as aresll ofthe movernent of protons from one waler molecule to another (Figure 2-15B). By raion. the HsO" concentration ‘s usually referted to asthe #” concentration, even though most protons ‘ivan aqueous solution are present as H:O". To avoid the use of unwieldy ‘numbers the concentration of Bis expressed using a logarithmic scale called the pH scale Pure water has a pH of7.0 and is thus neural—that |, neler acidic (pH <7) nor basic @H>7) [Acids are characterized ns being strong or weak, depending on how readily they give up thei protons to water. Strong aids, such 25 hydro chlone acid (HC), lase their protons casly Acetic acid, on the other hand, is a weak acid necsuse it holds on tots proton fairy tightly when cisslved in water. Many ofthe sci important inthe cell—such as mol- {ecules containing 2 carbonyl (COOH) group—re weak acid (see Panel 2-2, pp sé), Their tendency to give up 2 proton with some reluctance 's expoted n a varety of cellular reactions: ‘Because protons can be passed reallly to many types of molecules in cells, thus altering te molecules’ characters, the H concentration inside ‘acell—ts pH must be closely controlled. Acids wll ive up their protons ‘more readly ifthe H* concentration is low (and the pH is high) and will Dold onto ther protons (or accept them back) when the H* concentration ‘high (and the pH is low naa ChemicalBonds 49 ‘igure 215 protons move contnously {rom one males to snother im aqueos Solon.) Tho rearuon ra kes aoc Sihonameletda sone soc casos" ster At pH 7 near al ofthe est 300 redefine ronal neato (Glare moleales ar caranualy ‘nefangna enh eo oer frm CoyCCHAPTER2._Chamical Components ot cas Figure 2-16 In aquoous saltors, the oncarration of hyaroyl (OF on Increases a the concenrason of HO" (orn) ione deersaens Ine pneu ‘ho twovalegs fOr x iH away 1 (rolean® Atrewval oe (OH Src both one are preset 107 ASO Syma narpon ct conan sess Songun fer aperocmate pr values. QUESTION ‘A. re thors HO" ions prosot in ‘ure water at neutral pH Ge, t pH STO Iso, how are thay formed? B. Wthey exist hat ithe rti ‘oF H40" lane to HO motels pautal pH? Hin the molecular weight oF waters 18, and 1 ter of water woigns 1g) ler | the 3 1 [bak oe OO ma ee | [oe ssc] [D0 17 [sara oe ci 107 [erp rare C20) Molecules that accept protons when dissolved in water are called bases. Justa the defining property of an acid is that rases the conceniation | ‘of H30" ions by donating a proton toa water molecule so the defining ‘property of a base is that it raises the concentration of hydroxy (OH) fons by removing a proton ftom a water molecule. Sodium hydroxide (@8aOH) is basic the tem alkaline fs also used). NaOH I considered a ‘strong base because it realy disoclates In aqueous solution to form. Na" ions and OH fons. Weak bases—which have a weak tendency to ‘accep a proton flom waterhowever, are more important in cells. Many biologically important weak bases contain an amino (NH) group, which ‘can generale OF by taking 2 proton Irom waler:-NEy + Hj0— NH + (OH (eee Panel 2-2, pp. 6-69. Because an Olt ion combines witha proton to frm a water molecule, an increase in he Olt concentration forces a decreaee inthe Ii" concen ‘tation, and vice versa (Figure 2-16). A pure solution of water contains ‘an equal concentration (10-7 M ofboth fons, rendering it neutral pt 7) “The interior ofa cell's Kept close to neutral bythe presence of buffer. mixtures of weak acids and bases that wil adjust proton concentrations ‘around pli 7 by releasing protons (acids) ortaking them up (bases) when: ‘everthe pti changes. Ths gWve-and-take Koops the pt oFthe cell lately ‘constant under a varety of conditions SMALL MOLECULES IN CELLS Having looked at the ways atoms combine to form small molecules and how these molecules behave in an aqueous environment, we now exam- ine the main classes of small molecules found ia cells and their biological roles. Amazingly, we wil sce that afew basic categories of molecules, formed from just a handil of diferent cements, give sve to all the ‘extmordinay richness of fom and Behavior displayed hy living things. ACell Is Formed from Carbon Compounds lt we disregard water, nearly all the molecules in cll ate based on car- bon. Caron is cutstaning smong al the elements in ts abt to form large molecules: Hecause carbon atom is small and has four electrons and four vacancies in ts cuter shel i readily forms four covalent bondswith other aloms (see Figure 2-9) Mest importantly, ane carbon atom Can link other carbon atoms trough highly stable covalent C-C bonds, producing rings and chains thal can lorm the backbone of complex mol- ‘cules with no obvious upper imi to their size. These carbon-containing compounds are called organic molecules. By contrast, all ether mol- ‘ecules including water, ate sad o be inorganic. In acition to containing carbon, the organic molecules prodiced hy cells Iequenty contain spectie combinations af atoms, such as the methy [Ely Bjdo3y -Ol), carboxy! -COOH), cartons! EC-O) phosphony {802 and amino (-NH,) groups. Fach of these chemical groups has distil chemical and physical properbes that inluence the Behavior of the molecule in which the group occurs, including whether tbe molecule {ends lo gain or lose protons when dissolved in water an with which ther molecules it wil interact. Knowing these groups and their chemical properties greatly simples understanding the chemistry of life. The most ‘common chemical groups and some of thei properties are summarized inPanel2-1 (pp 66-67. Cells Contain Four Major Families of Small Organic ‘Molecules: ‘The small organic molecules of the cell are carbon compounds with molecular weights in the range 100-1000 thal conlain up to 30 er so carbon aloms. They are usually found free in solution inthe eyiosol and hhave many diferent roles. Some are used as monomer subunis lo con siruct the cells polymeric macromolccues—is protelns, nucleic adds, land large polysaccharides. Olhers serve as enetgy sources, being bro Keen down and transformed into clher small molecules in a maze of inlracellular metabolic pathways. Many have more tran one ole inthe cellacting, for example, as both a poteiial subunit for a macromol ‘cule and as an energy source. The small organic molecules are much Jess abundant than the organic macromolecules, accounting fer only about one-tenth of the total mass of ganic matte in a cell But small ‘xganiec molecules adopt a huge variety of chemical forms. Nearly 4000 diferent kinds of small organic molecules have been detected in the ‘well studied bacterium Escherichia col All organic molecules are synthesized from—and are broken down intowathe same set of simple compounds. Both their sylhesis and their breakdown occur through sequences of simple chemical changes that are limited in varety and follow step by sep rules. As a consequence, the compounds in cell are chemically related, and most can be clas: ied into a small number of distinct families. Sroadly speaking, cells conlain four major families of small organic molecules: the sugars, the fly aids, the amino acids, and the nucleotides Figure 2-17). Akhough ‘many compounds present in cells do not Ht into these categories, these ‘our families of small organic molecules together with the mactomol ecules made by linking them into long chains account fora larg frac tion ofa cell's mass (Teble 2-2) et aa i | ‘smal Molacules n Calis ‘igure 2-17 Sugars, faty aed, amino meas hoy for te morarene Dulin lees, or stones, rrr Ongena othe ‘mSzonolecdse deter ola ‘Ssembtes of Mecll some ete sugars nd ay aed 0 a0 onary sous,‘CHAMTER2 Chomical Components oto $Thonocechande, on bo roposntad In Several ways (8) smut rms Roche dove me hove seve bol eactogetarby si nee ‘Swann tne eset Coe Te ‘Redken ies ae usedto neste he ple Glia sugartng and show hat he=H fd ort cup ae nt he sara pane 2 ‘Barna Arter of ctor Gussernaz cies warconavaton™ Gxtaland ack mosaln wie he ‘tree dmensonelarangamartof the atoms inipace s nseatan (arpa Inada hid ae wal ar dopcing te bo (Srontcnalnrangerent cf tests, sh howe roavoruor ndeuoce contour fine moinese owe 29) Teastonein ©) ra @)ze cred seh gue 29 hk ita Od Ts a consntaral Co TABLE 2-2 THE & £ f i 1 i 8.828882 - hosts 2 azomolecos uct ac, a ‘tang andpoyescchre here a fe dae of hoppy 8c whch es mary aes |(oiscussad in Chapter 4). re ™ ‘Sugars Are both Energy Sources and Subunits of Polysaccharides ‘The simplest sugars—the monosaccharidesate compounds with the ‘general formula (C#0)n, where n is usually 3, 4, 8, of 6. Glucose, for ‘example, has the formula Cakis0. (Figure 2-18). Because ofthis simple orm, sugars, and the larger molecules made ffom them, ae called ‘arbolytrates. The formula, however, does not adequately define the ‘molecule: the same set of carbons, hydrogens, and oxygens.can be Joined {agether by covalent bonds ina varity of ways, creating tuctores wth sifferent shapes. Thus glucose ean be converted int = cifeent sugar— ‘mannose oF galaclosesimply by switching the orientations of specie “OH groups relative lo the rest ofthe molecule (Panel 2-t, pp. 7273) ‘naddion, each of these sugars can exist in eliher of two forms, called the form and the form, which are miror images of each other. Seis ‘of molecules with the same cheaical formula but diferent structures _are called isomers, and miror-image Pals of such molecules are called gue HOH 6 oo‘ptcal isomers. womers are widespread among organic molecules in general, and they lay 2 major pat in generating the enormous vaiely Cofsugars. A more complete ouline of sugar sutures and chemistry fs presented in Panel 2-4 ‘Monosaccharides can be linked ty covalent bonds—called glycosidic bbonds—to_ form larger carbohytrates. Two monosaccharides linked together make a disaccharide, such as suctose, which Is composed of 2 glucose and a fructose unt. Larger sugar polymers range from the falgesoccharies (risacchandes, tcirasaccharies, and s2 on) up 10 fiantpotisacchandes, which can contain thousands of monesacchande subunis (mono). In most case, the prefix oligo is used to refer to ‘molecules made ofu small numberof monomer, typically 2 to 10 inthe ‘ave of oligosaccharides Polymers, in contrast, can contain hundreds or ‘thousands of subunits. “The way sugars are linked together llusrales some commen features of biochemical bond formation, A bond is formed between an -OH group ‘none sugar and an 01 group on another by a condensation reaction, ‘in which a molecule of water is expelled asthe bond is formed (Figure 2:9) The subunits in ctherhiologisl polymers, including nucieic acids land prteins ae aso linked by concensation reactions in which water {is expelled. The bonds created by allel these condensation reactions can be broken bythe reverse process of hydrolysis, in which 2 molecule of water is consumed. Generally speaking, condensation reactions, which sgihesize lager molecules fom smaller subunits, ate energetically ‘unfavorable; hydrlysss reactions, which break down larger molecules into smaller subunits, are energetically favorable Figure 2-20), Because each monosaccharide has several ee hydroxyl groups that can form a link to another monosaccharide (orto some other compound, sugar polymers can be branched, and the numberof possible polsac- charide structures I extremely large. For this reason, i fs mich mone ‘Scull to determine the arrangement of sugars ina complex polysacch=- ‘ide than isto determine the nuclectide sequence ofa DNA molecule or the amino acid sequence ofa protein, in which each unis joined tothe next in exaclly the same way. ‘The monosaccharide glucose has 2 cenlral role as an energy source for cells, a5 we explain in Chapter 13. lisbroken dawn te smaller molecules ina Series of reactions, releasing energy thatthe cell can hamess (0 do ‘useful work. Cells use simple polysaccharles composed only of glucose ‘uits— principally eigen n animals and starch m plants~as long-term ‘Sores of glusase, held in resenve for energy production ‘Sugars do not function exclusively in the production and storage of energy. They are also used, for example, to Make mechanical supports ‘The mast shundant organi molecule on Earth-—the cease tat forms plant cel walle—is a polysaccharide of ghicase. Another extraordinarily bundant organic substance, the cin of insect cxeskeletons and fungal fell walls is also a polysaccharide—in this case, a linear polymer of Sugar devvatve called N-acevlglucosamine (see Panel 2-4, pp. 72-73) Other polysaccharides, which lend tobe slippery when wet, are the main components of slime, mucus, and gisle. no wo en 0c ew — A eo =e =< SmotMolacuesin Cals 88 ©, + fon wo corey momma Smugremeseniece, Pesci gee See ee poems omer oa Elcegwaasen ESSN sfeisckgeumciaaatCHAPIER? Chemical Components of Cas gre 2-21 Fatty acids have both “aonic ad se aon cy necr he tsoest Rtocaton aerate sadshown et Sra oman sg TeagienSioai ganna fim hoaaeinnser pH eat Sed mode specs hrg model tron ‘smaller oligosaccharides can be covalently lnked to proteins to form ay copra, r to lipids to fonm glycolipids Panel 2-8, pp. 74 75), which are both found in cell membranes. The sugar side chains atached to ighcoproteins and glycolipids inthe plasma membrane are thought to help protect the cell surface and often help cells adhere to one another. Dillrences in the types of cell-surface sugars form the molecular basis {br the human blood groups, information that dite which blood ies can be used during wanstusions. Fatty Acid Chains Are Components of Cell Membranes ‘A faty acid molecule, such as palmitic acid, has wo chemically distinct regions. One is along hydrocarbon chain, which is hydrophobic and not Very eactive chemically. The other isa carboxyl (COOH) group, which behaves as an acid (carboxylic acid: in an aqueous solution, I is fon- ied -COO), extremely hydrophilic, nd chemically reactive (Figure 2-21). Molecules—such as flly acidsthat possess both hydrophobic and hydrophilic regions are termed amphipathic. Almost all the fally acid ‘molecules in a cell are covslenty linked to other molecules by thei ear boxgiic acid group (ce Panel 2-5, pp. 74-75), ‘The hydrocarbon tall of palmitic acd Is sure: thas no double Bonds between its carbon atoms and contains the maximum possible number of hydrogens. Some other fatty acs, such as oleic acid, have unsatu ‘uted tals, with one ot more double bonds along thelr length. The double bonds create Kinks inthe hydrocarbon tals interfering wih ther ably Uo pack together. Fally acid (ais are found in cell membcanes, where the lightness of thelr packing affects the fudily ofthe membrane. The ‘many diferent fay acids found in cells ifr only in the lengl of thelt hnydrecarbon chains and in the number and position of the carbon. catbon double bonds (sez Panel 25) fatty acids serve as = concentrate oor reserve in cells they an be bro- en donen to prostice about six times ss much usable energy, gram for sgom, as glicose fatty acids ae sored in the eytoplaem of many celle In the foo of fat droplets composed of tnagissero! molecules com Pounds made of thre fatty acid chains covalent joined to a glycerol ‘molecule (igure 2-22 and see Panel 2-8). Tacyigicerols are the an- ‘mal fats found in mest, butter, and cream, and the plant offs such as orn oll and olive oil When a cell needs energy, the fatty acid chains i ae eereresseesrsee BS 8can be released from tiacylgiyeerols and broken doven into wo-carbon Units These two-carbon unks are identical to those derived from the breakdown of glucose, and they enler the same energy-ieiding reaction pathways, 2s descrbed in Chapler 13, Fall acids and their derivatives, including iacylglycerols, are examples cf lipids. Lipids are loosely defined as molecules that af insoluble in “inter slunle in fat and organic solvents such a benzene. They Sp ‘ally contain long hydrocarbon chains, a5 inthe fay Sids, or multiple linked aromatic rings, as inthe steroids (sce Panel 2). “The most unique function of faty acid ie in the establishment ofthe iid bilayer, the structure that forms the basis fr all ell membranes. These (hin sheets, which enclose allcell and surround ther internal organelles, fate compose largely af phospholpus Figure 2-23. Uke triacyglycerols, most phosphaliptdsare constructed main from fatty elds and glycerol. in these phospholipids, however, the glycerol joined to two fatty acid chains, rather than to three a in tnylycerois The emaining “OM group on the glycerol s inked to a hydrophilic phosphate group, which in tum is atached toa small hydrophilic compound such as ‘choline (sce Panel 2-5, pp. 72-75). with ther two hydrophobic fatty acid fails and a hydrophilic, phosphate-contsining hea, phospholipids are SStongly amphipathic. his charactensic amphipathic composition and Shape gives them very different physical and chemical propetics from (atylglcerols, which are predaminanliy Ixrophobic. In addition (o ‘phospholipids, cell membranes contain dllering amounts of other ips, Inching phcolpids, which ate structurally similar to phospholipids but ‘contain one or more sugars instead of a phosphate group. “thanks to their amphipathic nature, pure phospholipids readity foem ‘membranes in water These lipids can spread over the surface of water fo form a monolayer, with their hydrophobic tals facing the sir and theit Inydrophlic heads in contact withthe water, Altemalively, (wo ofthese phospholipid ayers can readily combine ailto-al in water to fom the [Phospholipic sandach thats the lip layer (ace Chapter 11) seca ES ee seeigee ates ietioencies Ae‘CHAPTER? Chemical Componants o ets Figure 2-24 Al amino acide have am “mine group, 3 carboxyl group, and 2 Sido chan (attached to tha =-arbon ‘fom intcal anesthe eoseto Jt wine ed ous tha onaed ‘am: wan ey re earned te Spoypenace can the changes on her Sruno acdstown eine ono of Srplet smo ade where sree Sep ey acne ctan ea ‘ru & hghthtacin io ante aren grou red EA babar ‘del ate (aspacotbngmodlat “nip hard ben atom Bue nde 6 sam sro we el Og-ay-onn-Ne on! i ct nysiow Ona he Sie so Fine a2 Sak ‘ry. thoariosed ade hare chown Sha thanc semua ctv pipepace ‘hank eappod by an arine gra, tocumbeotenratoal go, ‘he sequence ofomin secs ns protons sBbrevatedvang eters treesever ors no anor edo anata sogunea ays ‘easstreng for te Nsemne Gos ancl Shap oun mmasemriegven he euhca teatime EN « Amino Acids Are the Subunits of Proteins Amino acids are small organic molecules withone defining property: they al possess 2 carboxylic acid group and an amino group, both attached to a central -carbon atom (Figure 2-28). This carbon also cares a speci she Chain, the idenlity of which distinguishes one amino acid ‘fom another Cells use amino acids to build proteins polymers made of ana sci, ‘which ate joined head-to-tail im long chain that folds up into a thece- ‘imensional structure tha is unique to each ype of protein. The covalent ‘bond hetweon two adjacent amine acids na protein chain Iscalleda pep ‘ide bon, andthe resulting chain of amino acids | therefore also known ‘8a polypepide. Peplide bonds are formed by condensation reactions that link ene amine acd to the nex. Regardless of the speci: amino ‘acids from which itis made, the polypeptide always has an amino (XH) ‘group al one endl N-lerminus—and 2 carboxyl (COOH) group st ils ther end—ils C-terminus (Figure 2-25). This dillrence i the two ends [Bves a polypeptide definite cirectionalty--sstrustura fas opposed #9 lectricab polarity ‘Twenty ypes of aminoacids are commenty Sound in proteins, each with a lilrent side chain allachedto ts ecarbon aor Panel 2-8, 9. 76-77) How this precise sel of 20 amino acids came to be chosen is one one msteries| Surmuncing the evolution of ie, there fo obvious chemical eaeom Why ther amino ids could not have served just as well But once the selection ‘had boon locked ito place, I cud not be changed as too much chemistry Jad evolved to exploit. Swfching the types of amino acids used by clls— ‘whether bactenal, plant, oF animal woud require the organism toretco ts ‘are metabolsm to cope wih the new bulng blocks. Like sugars, all arsina acids (except glycine) exist as optical isomers termed b- and forms (see Panel 2-6) But only forms are ever found in proteins (although amino acids eccur as part of bacenal cell was ‘and in some andbitics, and »-serine Is used as 2 signal molecule in the brain. The ongin ofthis excusive use of amino acids to make proteins ‘is another evolutionary mystery. “The chemical versity that the 20 standand amino acs provide is italy important to the function of proteins. Five ofthe 20 amino aciés—includ- ‘ing lysine and glutamic acd, shown in Figure 2-25—have side chains ‘that form jons in solution and can therefore carry a charge. The others ‘ate uncharged. Some amino acids ate polar and hydrophilic, and some {ate nonpolar and hydrophobic (see Panel 2-6). As we discuss in Chapler 4 the collective properties of the amino acid side chains underlie all the clverse and sophisticaed funcions ef proteins. And proteins, which con- Silte half the dry mass of cell, eal the center of ife's chemist. Nucleotides Are the Subunits of DNA and RNA DNA and RNA are buil from subunits called nucleotides. Nucleotides ‘consist of nitrogen-coniining ring compound linked lo five-carbon‘Small Molecules in Calls 87 igre 2-26 Adenosine triphosphate (rics cntly penn (Senor coke steal or Inahche tee soso rau, ‘Jochaedn yo The presen of ro oe gap on tesco con of ‘Re aigsr mg (ed) seungushes ie Suge serene @ l-oestek mode (ovo 23} ing ta rata re yoiou, ‘The nitrogen: containing sings all these molecules ave generally referred {os buses for historical reasons: under acidi: conditions, they can each bind an #° (prton) and thereby increase the concentration of OH ions in aqueous solution. There sa strong family resemblance between the dillerent nucleotide bases. Cylosine (Q),dnymune (1), and wae (U) are called pyrimidines, because Uy all desive [om a si-membered pyrimi- dine ring; uarine (6) and adenine (A) ate purines, which bear a second, fivesmembered ring fused to the scmenshered ring. Fach muclenide is ‘named after the hase it contains (sce Panel 2-7, pp. 78-79). A hase plus its sugar (without any phosphate group attached) icaled 2 nuclease. "Nucleoside dl-and phosphates can act as short-term carers of chem- cal energy. Above all others, the rbonucleoside triphosphate known {a adenosine triphosphate, or ATP (Figure 2-26), partiipates in the luansfer of energy in hundreds of metabolic reactions. ATP is formed {rough reactions that are driven by the energy released from the break- down of foodstuls. 1S three phosphates are linked in seres by two ‘phosphoanhyaride bonds see Panel 2-7). Rupture of these phosphate bonds by hydroyss releases large amounts of useful energy, aso known as fice energy (see Punel 3-1, pp. 94-96). Most often, iis the terminal phosphate group that is spit offor transfered to another molecule— fo release energy that can be used to drive biosyihee reactions (Figure 2-27). Other nucleotide derivalives serve 2s carriers for ether [chemical groups. Alo hi s desenbed in Chapter 3 ee thle “- IRSA Fg 2 ate om ADP M40 fei | intganc pupusa eesti Storgy hon ti crohaod back to ae ‘ADP andinorgani phosphate, Te =) ‘Saud or at aptiente ces om ler the or Yatng oon ot we ‘cert in sara ele ing ond zome Scum ote prs care SES ne hohe ot [tron energy ta see ‘many process ne cele logater the ro ctene um fom be Pople ect)CHMSIER 2 Chemica! Components of Cale = eo eeieoecy oe Sie aeanee, pectin on eee eee Zoaaeeieees oe Soteoaben Sea Nucleotides also have a fundamental role i the storage and retrieval of ‘ological information. They serve as busting blocks for the construc tion of nuctsc aids—long polymers in which nucleotide subunits are linked by the formation of eovalent phosphodiester bonds between the ‘Phosphate group alached tothe sugar of one nucleotide anda hydroxy ‘group on the sugar of the next nucectie (Figure 2-28). Nuceic acd ‘chains sre symthesind from energy rich nileoside triphosphates by | condensation reaction that releszes inorganic pyrophosphate curing ‘Phosphodiesler bond formation (see Panel 2-7, pp. 78-73). “Thetearetwo main types af nucleic acs, which dif inthe typeof sugar macoolseis es paynersomred ‘fom mal mises (lecsmonomers or sbunds a ike SSpultrty cordon once frganic monomers. or subunits, inlo long chains, or polymers (Figure 2°30 and How We Know, pp. 60-61. Yet they have many unexpected properties thal could no have been predicted from their simple consis nls For example i leok 2 long Lime to determine that the nucleic acids, DNA and RNA, slore and transmit hereiary information Gee How We now, Chapler§, pp. 193-196), Proteins are especially versatile snd perform thousands of dstinct func ons. Many proteins ct as highly specie enzymes that catalyze the chemical reactions tht take place in cells. For example, one enzyme in plans, called ibulose bisphosphate carboxylase, converis CO> lo Suga, thereby creating most ofthe organic maller used by the rest ofthe ving ‘world Other proteins are used to build structural components: tubulin, for ‘ample, self assembles to make the cells long, silf mkrotubules (see Figure 1278), and histone proteins assemble into dsc-ke structures {hathelp wrap up the cells DNA in chromosomes. Yet ther proteins, such ‘ssmyesin, acl as molecular motors to produce force and movement. We ‘amine the molecular basis for many ofthese wide ranging funcons in later chapters. Here, we consider some of he general principles of macto- ‘molecular chemisty that make allo these actives possible. Each Macromolecule Contains a Specific Sequence of Subunits, Although the chemical action fr adding subunits to each polymer are ferent in detail for proteins, nucieic acids, and polysaccharides, they share important featutes. Each polymer grows hy the addition of 2 mono- mer onto one end ofthe polymer chain via a Condensation reaction, in which a molecule of waters lost for each subuni that Is added (Figure 2-31). nall cases, the reactions are catalyzed by specie enzymes, which ensure that only the appropriate monomers incorporated. ‘The stepwise polymerization of monomers into a long chain a simple way fo manufacture a large, complex molecule, because the subunils are added bythe Same reaction performed over and over again by the same set of enzymes. In a sense, the process resembles the repelilve opera tion of 3 machine in a fatory—with some important diferences. First, {par fom some ofthe polysaccharides, most macromolecules are made fom a set of monomers that are slightly diferent fom one another for ‘example, proteins are consircted ftom 20 diferent amino ack (see Panel 2-6 pp. 76-77) Second, and most important, the polymer chal is ‘not assembled at random from these subunits, nsiend, the subunits are ‘aes in a patcular onder, or sequence. “The biological functions of proteins, nuclete acids, and many polysac~ charides are absolutly dependent on the particular sequence of Subunits In the linear chains. By varying the sequence of subuits, the cell could 1m principle make an enormous diversity ofthe polymeric molecules. “This for a protein chain 200 amino ackls long. there are 20° poss ble cominnations (20 20» 20 20. mulpied 200 times), while For a [DNA molecule 10,000 nucleotides long (small by DNA standards), with ‘ts four different nucleotides, there ae 4160 diferent possbities—an “unimaginably lrge number Thus the machinery af pelymerzation mst ‘Macromolecules Cots igus 2-31 Macromelacle 0 frmed by dang subunit te one nd of han. Inseonaeneston ean, smoees (haste lat wth tne adaton ofeach foromer'e orsendof te gomrg cn ‘Frsvevote accion the eel the paljraroccusby be ston cf wor yboien Sow als Pepe 20“ HOW WE KNOW THE DISCOVERY OF MACROMOLECULES ‘The idea thal proteins, polysaccharides, and nucleic acids are large molecules that are constructed from ‘smaller subunits, inked one aller another into long ‘molecular chains, may seem fairly obvious today. But this was not always the case Inthe early part of the ‘wenfith century, few scientists beloved in the exist- ‘ence of such biological polymers bul from repeating Unis held together by covalent bonds. The notion that ‘such “righteningly Large” macromolecules could be “Sssomble rem simple building biocks was considered “downmght shocking’ by chemists of the day. Instead, ‘they thought that proteins and cther seemingly lange ‘organic molecules were simpy heterogeneous aggre {gales of small organic molecules held together by Weak “association forces" (igure 2-32), ‘The fst hint that proteins and other organic polymers ‘are lage molecules came from observing thelr ehav- lor in soluion. At the Um, scientists were working ‘with various proteins and carbohydrates derived from fodstus and other organic materials—albumin from egg whites, casein from milk, collagen ffom gelatin, ‘and celuloce from wood. Thelt chemical compositions ‘seemed simple enough: ike other ganic molecules, they contained carbon, hydrogen, oxygen, and, in the ‘ease of proteins, nilrogen. Bul they behaved oddly in Solution, showing, for example, an inabiily Lo pass ‘through a fine filter why these molecules mishehaved in solution was a puzzle. Were they really giant molecules, composed ‘of an unusually large number of covalently linked ‘atoms? Or were they more like a collodal suspension ‘of particles—a big. sticky hodgepodge of small organic ‘molecules that associate only iooscly? ef, W Ne ‘Sonat or Many tases founsin cesar paral ascites wih ios ‘ean ah amino group 9), whch Pasa weak nsny crevoby capt so ion rate ery Inceasing a concantrson of ee OH ins Ny ee NS7 PANEL 2-3 tHe principal types OF WEAK NONCOVALENT BONDS BONDS ‘rset nmr win tat motes ough {ire pe of hertnge aac frees troun ‘ractns anamyogen ons The epson ot ‘rhrseone sta ere tsing tages meron '35b00g covert bond. They ate Song ancugh provide ‘GgncUnang ony wn many of fomed ‘Sutanenaly HYDROGEN BONDS ‘Asaleasy csv water e Fan! 22 op 680, "ycrogen onc form when 3 hyaregen acm “endian oo ero ang Ras (anual ugg nage. ycrogen bo ate stenget when the tres tems ate Imaseoanene: Noswimmo. —ymunc” beanpis mn macmcecues ‘amin asin peypepde can can be drogen Bonded {pehernaoted poten \VAN DER WAALS ATTRACTIONS. Irmo atoms ae 0s tgeme, hy ent en te ‘Taheas hone wma tecrasun Te marc Sia eternal sk ‘Rete tn meme ot ®©@ee ineitvayoitscarane bennen nar ‘a Atoogh te re nda ver west, CGnacrwoae actors tan bone tnporait nen ‘ro macomolecar race egeee ver cee, “ie mat hen to stom tom consent ben, he cities tthe same ats sr ns ce ‘nun cera nan ne mone a et HYDROGEN BONDS IN WATER ny two tama hat can orm hytogen bond aaah other {an aternanvet form nyronen does water makes Ertan ofthe compostan nk water melo te Iarogen porate m vate between wo pte Don, adELECTROSTATIC ATTRACTIONS ELECTROSTATIC ATTRACTIONS IN WATER “ly argo groups Gon bond) ad btn arly charges woubs on ptr melee —Oni@— Guzoan 8 apd fas off pty 3th ‘astone betwean tne oaroesincesas por Ine absnce of water onc bond ae ver steng. ‘Tyas report forthostangthaush (ne 2 marble ae gat, aaa ays “eatin m commen abe NaC bona Sealy Gaus puto om waa.2 PANEL 2-4 an outune oF some OF THE TYPES OF SUGARS Pees Mopotacharges male the goerl onda (CO)y wher ncan be 4506 and hae two cr mate hye ru “hoy er contain an hyde group (=<) and ae cd aos or axetone poup(Se~e ] and are caled ketete sexnen rose canon mesos ING FORMATION Inaqueous ston the aldehyde or ketone group of sugar ‘mote tend to rant wth pony goup of hasan ‘molecule, Hereby Soong te mole into = MD“@ AND B LINKS. ‘SUGAR DERIVATIVES ‘Tenant tous on me carbon tat aes ne ‘enyroenorcups ot Boahyleot atone an pay ange Fam ce inplomencnacharse, OH bustionto the other The wo peorsarecaiea WM) Sunes glucose. an be cnt. Feplceaby other e-als, = hrc soon atone sar itnkad ts another. thew of Mecpgucnanne fe Boom omn ouneness saccuannes ease ane tine woo melee a oe mirece ee [a ieee eee von nc ‘OLIGOSACCHARIDES AND POLYSACCHARIDES Ling: rer 2d rence molec can be mad from ipl repeating age wba. Stor hans are cle o0gcaccaries ad long has ae cep nacre. ‘iynges for earpl,b pachaie mate ay of gure buns ne eget ‘COMPLEX OLIGOSACCHARIDES gion [Showapettve Mary arent ‘Sanyo pots ots, ‘Bistmscigesscnanie wih s seinen ora i Pe Coren g” PANEL 2-5 sary acios ano orHer LiPios Eunz Hares of emerent na of oy 20e ext Some nav neo more double Bran tar AN ay ah fove acon! (roi hore waa ora ‘ctor tal tte ce er geo wok ‘is dole bons ee radar ets Mee me iterative cnn be Pere Fay ace ar ster incl 22 ery zane {ata os trough ah ener mane © ren tofarm anise NAAR j 0 Pee ERE ‘cARBOXYL GROUP PHospHourIns Resist the ma cortor ton te carton grup ots ‘ay zed be zed ‘ Wow ‘e DAA Note phcsonoii tu ot te of arouse Syearlsreinkedto ty cule the ne Ow groan. ites topnosenet 2 The pooriens wih rie create ders forte tricdiooneor sve of al pol run such aserainepio AGGREGATES POLYISOPRENOIOS omen say nnn spec ‘ acetate eae | do ‘im ora pres a “Ther derivatives can form arger aggregates held together by roo forces “Tragiaycerosfom ae, spherical Prosi and alin fom sessing Hed {f2tcoplcs inte callteptam ays whore De ba fr ll mombrones OTHERLIPIDS ola tat re sous in oraarie ‘Tn Fr sttercoman era is ye sso snd potyooronclds Bot are7% PANEL 2-6 te 20 amino aciDs FOUND IN PROTEINS EAMles oF BASIC SIDE CHAINS AMINO ACIDS ‘econmon no st sor) Be owes sauna 4 Serre } en ev Bh rgd er o nd ae onl pap ‘oouralpe PEPTIDE BONDS In protins amino ads ar oinestogetherby an “The four atoms noes in ech pete tons fom 2g {a nage, aes eta Diora unt econ. Tera atten aroura te CH Band. ‘ram aeasinuedoy (opie bond an hey Eesha en seis eto ly cry CES)NONPOLAR SIDE CHAINS | i i UNCHARGED POLAR SIDE CHAINS ‘ACIDIC SIDE CHAINSPANEL 2-7 asurvey oF THe NucteomipEs PHOSPHATES. “Th phosphates te normaly ras to “ec hyron ofthe bos or Seoeyese ox (Sesonsted 7. Mono, (and tpmospates re commen ea BASE-SUGAR. Anudeatda consss of 2eivogencontaning ful UNKAGE base. a ecarbon spar none or more phosphate wuss, ‘ebwed oy pime mak eters oe Seat Fhe "Sprmacieen” ctNOMENCLATURE Tenamercan be confining bl the rrr les, [Meevtedts teecaptal eters, Sam apie tou nace econ AUP. adenosine monopole ‘aon decnyeseosie onephosate or” Sarai achoshate ir TSdanesnetrpoospe NUCLEIC ACIDS Tetornicecaaspehmers mceosst ‘Sotrbrten mes? caer ‘ewece of cetern sac ea NUCLEOTIDES AND THEIR DERIVATIVES HAVE MANY OTHER FUNCTIONS a recaoie ch and viphoipaty hey cary comical erargy nthe ‘Ssiy narotze posshosmyarce bons, exam: arr or oH oe ample conzyme ACoA) c fs @ reve wes sens eseane stra maleue nec example Me Coe)