CARBOHYDRATES  Cn(H2O)  1:2:1 (1C: 2H: 1O)

** Look for functional groups: 1) Aldehydes 2) Ketones 3) Alcohols

I. Nomenclature AND Classification, Common names:

** Named based on:
 Length of carbon chain
 Functional groups present on sugar
 Stereochemistry of sugar

 What 3 things must a molecule have to be classified as carbohydrate?

o 1) 3-carbon backbone
o 2) Aldehyde OR ketone group
o 3) @ least 2 hydroxyl groups


 Hydrates of carbon  can be named according to # of carbons it contains
o Cn = # of carbon atoms w/ matching H2Os

 Carbohydrate = sugars, monosaccharides, disaccharides, polysaccharides

 Carbonyl carbon = MOST oxidized = ALWAYS have lowest possible #

 MONOSACCHARIDES= single/simplest carbohydrate unit

o Aka = simple sugar
 SAME kind of molecule
 Simplest monosaccharides  trioses
o Common names: triose (3 carbons), tetrose (4 carbons), pentose (5 carbons),
hexose (6 carbons)
o -ose = denotes sugar
 Aldose = aldehyde sugar (aldehyde group = most oxidized functional
group)
 Ketose = ketone sugar (ketone group = most oxidized functional group)
o Include:
 Glucose
 Fructose
 Galactose
 Ribose
 Xylose
 Disaccharides = 2 sugars bound together
 Polysaccharides = long sugar chains for glucose storage (i.e. glycogen in animals, starch
in plants)
 Absolute configuration:
o Describes spatial arrangement of atoms OR groups around chiral molecule
o Assign priority to substituents of chiral carbon
  HIGHER the atomic #  HIGHER priority
 Orient the molecule with the LOWEST priority substituent in the back
 CLOCKWISE = R
 COUNTERCLOCKWISE = S

 Basic structure of monosaccharide => GLYCERALDEHYDE

o Polyhydroxylated aldehyde = aldose aldehyde sugar

 Simplest aldose (Aldotriose)

 Cyclic structure:
o Monosaccharides can undergo INTRAmolecular rxns to form RING structure
o Cyclic rings = stable in solution and can form 2 types of rings:
 1) 6-membered rings  6 carbons in ring = PYRANOSE
 2) 5-membered rings  5 carbons in ring = FURANOSE
 Glycosidic linkages:
o Covalent bonds B/W monosaccharides AND alcohols
o Aldehyde carbon  participate in glycosidic linkages
 Sugars acting as substituents via linkage => Glycosyl residues
o When alcohol is another monosaccharide, produces a disaccharide
 Examples:
 Sucrose
 Lactose
 Maltose
 Cellobiose
o Linkage b/w C1 on 1st sugar AND C2 on 2nd sugar
=> 1,2 linkage
o Linkage b/w C1 on 1st sugar AND C4 on 2nd sugar
=> 1,4 linkage
o Linkage b/w C1 on 1st sugar AND C6 on 2nd sugar
=> 1,6 linkage
  May also be classified as alpha OR beta:
o Hydroxyl group on C1 => oriented  UP = Beta (Birds fly in sky)
o Hydroxyl group on C1 => oriented  DOWN = Alpha (Fish swim in sea Down
under)
 PREFIX:
o Deoxy = has a -H in place of -OH @ certain position
o D/L = absolute configuration = assigned based on chirality of carbon atom
furthest from carbonyl group
o α/β = Anomeric configuration
 SUFFIX:
o ALL sugars end in -ose

FUNCTION: Role of carbohydrates and sugars

 1) Energy source/energy means energy stores (glycogen)
o Main energy source = Glucose
o Production of fats which are also used as energy source
o Energy stores => triglycerides
o Where do we get our sugar molecules come from?
 Produced by plants  capture energy stored in light  transforms energy
into chemical bonds w/in sugar molecule
 In sun have nuclear rxns taking place and release energy that is stored in
EM waves that propagate through space and makes way to plants
  Plants take CO2 and H2O and use energy stored in light to produce sugar
molecule + O2 (use in ETC in process of aerobic cellular respiration)
 Ingest carbohydrates produced by plants  break down carbohydrates into
individual monomer sugars (if not glucose molecule then transform into
glucose molecule)
 If have too many  glucose can be stored as glycogen
 Energy produced in nuclear rxn is stored in chemical bonds w/in sugar
molecules  ingest sugar molecules – take same energy from sun and
store in ATP molecules and use ATP to carry out processes
o But do NOT have as high concentration of energy per gram as lipids b/w do NOT
have as high concentration of C-H bonds

 Carbohydrates are produced by plants  ingested & broken down into individual
monomer sugars

 2) Formation of structural framework of Nucleic Acids

=> DNA & RNA:
o ATP contains a ribose sugar
o RNA & DNA: Nucleic Acids
 Store genetic information
 RNA = Ribose:  ribo-nucleic acid
o Ribo = ribose sugar = pentose sugar
o Sugar links nitrogenous base to
phosphate group
 DNA = DEOXYribose  deoxy-ribo-
nucleic acid
o 2nd C = NO hydroxyl group
o Deoxy = 2’H (vs. 2’-OH in RNA)
o Acid = phosphate group gives it acidity

 3) Cell walls of bacteria => Structural elements

o Bacteria
 = peptidoglycan OR murein
o Plants
 = cellulose
o Animals
 = chitin

 4) Lipid AND Protein Modifications:

o Linked to many proteins AND lipids
 Cell-cell communication AND interactions B/W cells and other elements in
cell environment
 o Use sugar to modify lipids and proteins  diversify the capabilities and functionality
of proteins and lipids by 
 Attaching sugar components onto macromolecules  by combining sugars
and proteins or sugars and lipids  increase capabilities of these
 Ex: Tissue factor (coagulation cascade)  is a glycoprotein that
interacts w/ other molecules = initiate formation of blood clot (intrinsic
pathway of coagulation cascade)
o Sugars make up components of cell walls

MODIFICATION OF CARBOHYDRATES:
 Monosaccharides may be modified via addition of groups

 2 modifications of sugars:

o 1) PHOSPHORYLATION of Sugars:
 When cells uptake sugar molecules  the 1st step in glucose metabolism is
to phosphorylate glucose
 Whenever a system in nature contains charge  means its energy =
HIGHER = LESS stable = MORE reactive
 By phosphorylating glucose molecule  G-6-P => INCREASE
reactivity of glucose molecule to be able to undergo further
processes
 INCREASE polarity of glucose molecule
 Phosphorylated glucose contains HIGHR charge = MORE polar
 MORE likely to spontaneously leave the cell
o b/c around the cell have cell membrane that contains
nonpolar lipid molecules, so HIGHLY polar glucose-6-
phosphate CANNOT spontaneously leave the cell b/c it
cannot pass across nonpolar bilayer membrane
surrounding the cell
 st
1 step of glucose metabolism  modifying glucose by ADDING phosphate group
o PHOSPHORYLATION of glucose gives => Net (-) charge => becomes anion
o Do this for 2 reasons:
 o 2) Glycosidation w/ Alcohols:

NUCLEOTIDES:
 Building blocks  and involved in cell’s use of energy

 Made up of 3 components:
o 1) 5 carbon (pentose) sugar
o 2) Nitrogenous base
o 3) Phosphate group

EPIMERS vs. ANOMERS:

o Epimers
o Differ in absolute configuration @ only 1 C  R or S
o Anomers
o Differ in configuration @ hemiacetal/acetal = anomeric C
 Note: Conversion B/W anomers = MUTAROTATION

GLUCOSE
 Carbon backbone = makes it organic

CARBOHYDRATES
 POLAR molecules
 Dissolve in polar solvents 
like H2O
 Form hydrogen bonds w/ H2O
molecules
 HYDROOHILIC
 o Mix w/ H2O
 2 functional groups:
o 1) Aldehyde
o 2) Ketone

1) ALDEHYDE:
 ALCOHOL =
o ANY organic compound in which hydroxyl functional group OH = bound to
saturated carbon atom
o ALL have suffix -ol
o Carbon
 => double bonded to oxygen
 => single bonded to hydrogen
o Formed by:
 Oxidation of alcohols

2) KETONE:
 Organic compound R1 and R2 can be variety of carbon containing
substituents
o Carbonyl “sandwiched” B/W 2 radical groups (R1 & R2)

 Carbohydrates are polyhydroxy aldehydes OR polyhydroxy

ketones
 Car being hydrated
o 3 girls = 3 atoms  C, H, & O
 OH my god! What a wet (H2O)  carbohydrates = hydrophilic
o Car has 4 wheels
 Carbohydrate = 4 calories/g  amt. energy in 1 g of carbohydrate
 Hose  suffix -ose
o Used in mono OR dia – saccharides
CARBOHYDRATES Right hand finger trick:
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