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
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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
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7.1 How Are Carbohydrates Named?

™Monosaccharides

™Oligosaccharides

™Polysaccharides
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7.2 What Is the Structure & Chemistry of

Monosaccharides?
™Aldoses

™Ketoses
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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
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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
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What Are the Structures of the Aldoses?

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What Are the Structures of the Ketoses?

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What Is the Pyranose (Cyclic) Form of Glucose?

™Alcohols react with the carbonyl groups of aldehydes to form
hemiacetals
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What Is the Furanose (Cyclic) Form of Fructose?

™Alcohols react with the carbonyl groups of ketones to form hemiketals
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What Is the Anomeric Carbon?

Anomeric Carbon –

Anomers –
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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)
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How Does a Pyranose Differ From a Furanose?

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What Are the Conformational Forms of Sugars?

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7.3 What Is the Structure & Chemistry of

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

Glycoside –

Glycosidic Bond –
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What Are the Common Disaccharides?

™Two monosaccharide units (residues) linked by a glycosidic bond
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What Is the Reducing End & the Nonreducing End?

Reducing End –

Nonreducing End –
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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
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What Is the Storage Polysaccharide in Plants?

™Starch (α-Amylose & Amylopectin)
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What Is the Storage Polysaccharide in Animals?

™Glycogen
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What Is the Most Common Structural Polysaccharide?

™Cellulose
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What Structural Polysaccharide Is Found in

Exoskeletons?
™Chitin
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What Are Glycosaminoglycans?

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What Structural Polysaccharide Is Found in Bacterial Cell

Walls?
Peptidoglycan –

Gram-Positive Bacteria –

Gram-Negative Bacteria –
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What Is the Difference Between Gram-Positive Cell Walls

& Gram-Negative Cell Walls?
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What Are the Structures of the Cell Wall & Membranes in

Gram-Positive & Gram-Negative Bacteria?
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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 –
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How Do Glycoproteins Interact With Membranes?

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How Does Glycosylation Affect Proteins?

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7.6 How Do Proteoglycans Modulate Processes in Cells?

™Proteoglycans – family of glycoproteins containing glycosaminoglycans
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What Are the Functions of Proteoglycans?

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