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Carbohydrates & Glycoconjugates of Cell Surfaces (Chapter 7)

Carbohydrates play important structural and functional roles in cells. They include monosaccharides, oligosaccharides, and polysaccharides. Monosaccharides can be aldoses or ketoses and exist in cyclic forms like glucose's pyranose ring structure. Oligosaccharides and polysaccharides are made of monosaccharide units linked by glycosidic bonds. Examples of polysaccharides include starch for plant storage, glycogen for animal storage, cellulose for structural support, and chitin in exoskeletons. Glycoproteins and proteoglycans are carbohydrates attached to proteins that influence cell structure and function.

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Marie St. Louis
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84 views31 pages

Carbohydrates & Glycoconjugates of Cell Surfaces (Chapter 7)

Carbohydrates play important structural and functional roles in cells. They include monosaccharides, oligosaccharides, and polysaccharides. Monosaccharides can be aldoses or ketoses and exist in cyclic forms like glucose's pyranose ring structure. Oligosaccharides and polysaccharides are made of monosaccharide units linked by glycosidic bonds. Examples of polysaccharides include starch for plant storage, glycogen for animal storage, cellulose for structural support, and chitin in exoskeletons. Glycoproteins and proteoglycans are carbohydrates attached to proteins that influence cell structure and function.

Uploaded by

Marie St. Louis
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© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
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Carbohydrates & Glycoconjugates of Cell Surfaces

(Chapter 7)
™Carbohydrates play a role in energy metabolism & storage, they are
building blocks of polysaccharides, nucleic acids, & glycoproteins, they
provide structural scaffolding for cell walls, and they are involved in
molecular recognition important in cell growth & transformation.
7.1 How Are Carbohydrates Named?
-monosaccharides, oligosaccharides, & polysaccharides
7.2 What Is the Structure & Chemistry of Monosaccharides?
-simple carbohydrates (CH2O)n that serve as building blocks (monomers)
-aldoses contain an aldehyde & ketoses contain a ketone
-stereochemistry, Fischer & Haworth projections, furanose & pyranose
7.3 What Is the Structure & Chemistry of Oligosaccharides?
-glycosidic linkage in disaccharides & oligosaccharides
7.4 What Is the Structure & Chemistry of Polysaccharides?
-polysaccharides contain more than 10 monosaccharide units
-storage polysaccharides are starch (amylase & amylopectin) & glycogen
-structural polysaccharides are cellulose & chitin
7.5 – 7.6 What Are Glycoproteins & Proteoglycans?
-glycoconjugates, O-linked & N-linked oligosaccharide groups
2

Carbohydrates & Glycoconjugates of Cell Surfaces


™Most abundant class of organic molecules in nature

™More than half of all organic carbon on Earth is stored in just two
carbohydrates – starch and cellulose

™Basic formula (CH2O)n where n ≥ 3

™Metabolic precursors to virtually all other biomolecules

™Breakdown of carbohydrates provides energy that sustains life

™Glycolipids and glycoproteins play important roles in structure and


recognition

™Characteristic Chemical Features of Carbohydrates


-one or more chiral (asymmetric) centers
-linear and ring structures
-polymeric structures via glycosidic bonds
-hydrogen bonding
3

7.1 How Are Carbohydrates Named?


™Monosaccharides

™Oligosaccharides

™Polysaccharides
4

7.2 What Is the Structure & Chemistry of


Monosaccharides?
™Aldoses

™Ketoses
5

How Does One Draw a Fischer Projection?


™Aldoses with at least three carbons and ketoses with at least four
carbons contain chiral centers

™Fischer Projection
convert to
CHO a Fischer CHO
projection
H C OH H OH

CH2 OH CH2 OH
D-Glyceraldehyde D-Glyceraldehyde
6

What Is the Stereochemistry of Monosaccharides?


™For monosaccharides with two or more asymmetric carbons, D and L
refer to the configuration of the highest numbered asymmetric carbon
7

What Are the Structures of the Aldoses?


8

What Are the Structures of the Ketoses?


9

What Is the Pyranose (Cyclic) Form of Glucose?


™Alcohols react with the carbonyl groups of aldehydes to form
hemiacetals
10

What Is the Furanose (Cyclic) Form of Fructose?


™Alcohols react with the carbonyl groups of ketones to form hemiketals
11

What Is the Anomeric Carbon?


Anomeric Carbon –

Anomers –
12

How Does One Draw a Haworth Projection?

CH= O CH2 OH
H OH H5 OH
HO H redraw O
H
H OH OH H C
5 HO H
H OH anomeric
CH2 OH H OH carbon
D-Glucose
CH2 OH CH2 OH
5
H5 O OH( β) H O
H
H + H
OH H OH H
HO H HO OH( α)
H OH H OH
β-D-Glucopyranose α-D-Glucopyranose
(β-D-Glucose) (α-D-Glucose)
13

How Does a Pyranose Differ From a Furanose?


14

What Are the Conformational Forms of Sugars?


15

7.3 What Is the Structure & Chemistry of


Oligosaccharides?
™Limited variety of monosaccharide building blocks polymerize to make
oligosaccharides and polysaccharides

Glycoside –

Glycosidic Bond –
16

What Are the Common Disaccharides?


™Two monosaccharide units (residues) linked by a glycosidic bond
17

What Is the Reducing End & the Nonreducing End?


Reducing End –

Nonreducing End –
18

7.4 What Is the Structure & Chemistry of


Polysaccharides?
Homopolysaccharide (homoglycan) –

Heteropolysaccharide (heteroglycan) –

™Polysaccharides can form linear and branched structures

™Functions
-Storage: Starch & Glycogen
-Structure: Cellulose & Chitin
-Bacterial Cell Wall: Peptidoglycan
-Recognition: Cell Surface Polysaccharides
19

What Is the Storage Polysaccharide in Plants?


™Starch (α-Amylose & Amylopectin)
20

What Is the Storage Polysaccharide in Animals?


™Glycogen
21

What Is the Most Common Structural Polysaccharide?


™Cellulose
22

What Structural Polysaccharide Is Found in


Exoskeletons?
™Chitin
23

What Are Glycosaminoglycans?


24

What Structural Polysaccharide Is Found in Bacterial Cell


Walls?
Peptidoglycan –

Gram-Positive Bacteria –

Gram-Negative Bacteria –
25

What Is the Difference Between Gram-Positive Cell Walls


& Gram-Negative Cell Walls?
26

What Are the Structures of the Cell Wall & Membranes in


Gram-Positive & Gram-Negative Bacteria?
27

7.5 What Are Glycoproteins, & How Do They Function in


Cells?
™Proteins covalently linked to oligosaccharide and polysaccharide groups
O-Linked Saccharides –

N-Linked Saccharides –
28

How Do Glycoproteins Interact With Membranes?


29

How Does Glycosylation Affect Proteins?


30

7.6 How Do Proteoglycans Modulate Processes in Cells?


™Proteoglycans – family of glycoproteins containing glycosaminoglycans
31

What Are the Functions of Proteoglycans?


™Proteoglycans may be soluble and located in the extracellular matrix or
they may be integral transmembrane proteins

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