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Carbohydrates: Structure & Biological Function (Chapter 7)

Carbohydrates play important roles in energy storage, structure, and recognition. They exist as monosaccharides, which can join together through glycosidic bonds to form disaccharides, oligosaccharides, and polysaccharides. Monosaccharides commonly exist as either linear or cyclic structures and include important subclasses such as aldoses and ketoses. Glycosidic bonds between monosaccharide units give rise to biologically significant molecules such as starch, cellulose, glycogen, and peptidoglycan. Glycoproteins contain covalently bonded carbohydrate units and are involved in processes like immunity, cell-cell interaction, blood clotting, and signaling.

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Marie St. Louis
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56 views

Carbohydrates: Structure & Biological Function (Chapter 7)

Carbohydrates play important roles in energy storage, structure, and recognition. They exist as monosaccharides, which can join together through glycosidic bonds to form disaccharides, oligosaccharides, and polysaccharides. Monosaccharides commonly exist as either linear or cyclic structures and include important subclasses such as aldoses and ketoses. Glycosidic bonds between monosaccharide units give rise to biologically significant molecules such as starch, cellulose, glycogen, and peptidoglycan. Glycoproteins contain covalently bonded carbohydrate units and are involved in processes like immunity, cell-cell interaction, blood clotting, and signaling.

Uploaded by

Marie St. Louis
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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Carbohydrates: Structure & Biological Function

(Chapter 7)
™Carbohydrates are the most abundant class of biomolecules. They play a
role in energy metabolism and storage, they are building blocks of
polysaccharides, nucleic acids & glycoproteins, they provide structural
scaffolding for cell walls, and they are involved in molecular recognition.
™Characteristics of carbohydrates: one or more chiral centers, linear and
ring structures, polymeric structures via glycosidic bonds, & extensive
hydrogen bonding.
7.1 Monosaccharides
-simple carbohydrates (CH2O)n (where n is 3 to 7) that serve as building
blocks (monomers) of more complex carbohydrates (polysaccharides)
-aldoses contain an aldehyde & ketoses contain a ketone
-Fischer projections represent the linear form of monosaccharides
7.2 Carbohydrates in Cyclic Structures
-the cyclic form of monosaccharides is favored over the linear form in soln
-furanoses are five-membered rings & pyranoses are six-membered rings
-Haworth projections represent the cyclic form of monosaccharides
-anomers (α & β) differ in stereochemistry at the anomeric carbon
2

Carbohydrates: Structure & Biological Function


(Chapter 7) – Cont.
7.3 Reactions of Monosaccharides
-monosaccharides form disaccharides by forming an O-glycosidic bond
-important disaccharides include sucrose, lactose, cellobiose & maltose
-nomenclature of glycosidic bonds (linkages)
7.4 Polysaccharides
-oligosaccharides contain 3 – 10 monosaccharide units.
-polysaccharides contains more than 10 monosaccharide units.
-Important storage polysaccharides include starch (amylose and
amylopectin) and glycogen
-Important structural polysaccharides include cellulose & chitin
7.5 Glycoproteins
-proteins that have covalently attached carbohydrate units & are involved in
immunity, cell-cell recognition, blood clotting & signal transduction
3

7.1 Monosaccharides
Learning Objectives: understand the fundamental structures, group classification &
stereochemistry of the monosaccharides
™Aldoses contain an aldehyde at carbon 1

™Ketoses contain a ketone at carbon 2


4

Aldoses
5

Ketoses

™EXAMPLE: Glucose is an:


a) Aldopentose
b) Ketopentose
c) Aldohexose
d) Ketohexose
™EXAMPLE: Fructose is an:
a) Aldopentose
b) Ketopentose
c) Aldohexose
d) Ketohexose
6

7.2 Carbohydrates in Cyclic Structures


Learning Objectives: be able to show the cyclization of monosaccharides to form
pyranoses & furanoses
™In aqueous solution, carbohydrates form cyclic structures with creation
of an additional asymmetric chiral carbon (carbon 1, anomeric carbon)
™Aldohexoses form pyranose (6-membered) rings
7

Carbohydrates in Cyclic Structures – Cont.


™Ketohexoses form furanose (5-membered) rings

™EXAMPLE: Circle the anomeric carbon in the two Haworth projections above
for fructose & for glucose on the previous page.
8

7.3 Reactions of Carbohydrates


Learning Objectives: know the fundamental reaction to form disaccharides
™Disaccharides & polysaccharides contain O-glycosidic bonds
9

Disaccharides

Reducing End –

Nonreducing End –

™EXAMPLE: What is the only nonreducing disaccharide on the previous page?


10

7.4 Polysaccharides
Learning Objectives: be able to recognize the structures & functions of polysaccharides
™Characterization of Polysaccharides
-the identity of the monomeric units
-the sequence of monosaccharide residues
-types of glycosidic bond linking the units
-approximate length (number of monosaccharides) of the chain
-degree of branching

™Biological Functions of Polysaccharides


-Storage: Starch

Glycogen

-Structure: Cellulose

Chitin

-Bacterial Cell Wall: Peptidoglycan

-Recognition: Cell Surface Polysaccharides


11

Starch (α-Amylose & Amylopectin) & Glycogen


12

Cellulose & Chitin (Structural Polysaccharides)


13

Summary of the Structures & Properties of Common


Polysaccharides
14

7.5 Glycoproteins
Learning Objectives: describe the structure & function of glycoproteins
™Glycoproteins have covalently bonded carbohydrate units attached via
amino acid side chains

™EXAMPLE: What are the general functions of glycoproteins. Provide some


specific examples.

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