Carbohydrates & Glycoconjugates of Cell Surfaces (Chapter 7)

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

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

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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Carbohydrates & Glycoconjugates of Cell Surfaces

Carbohydrates & Glycoconjugates of Cell Surfaces

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

Characteristic Chemical Features of Carbohydrates

7.1 How Are Carbohydrates Named?

7.2 What Is the Structure & Chemistry of

How Does One Draw a Fischer Projection?

What Is the Stereochemistry of Monosaccharides?

What Are the Structures of the Aldoses?

What Are the Structures of the Ketoses?

What Is the Pyranose (Cyclic) Form of Glucose?

What Is the Furanose (Cyclic) Form of Fructose?

What Is the Anomeric Carbon?

How Does One Draw a Haworth Projection?

How Does a Pyranose Differ From a Furanose?

What Are the Conformational Forms of Sugars?

7.3 What Is the Structure & Chemistry of

What Are the Common Disaccharides?

What Is the Reducing End & the Nonreducing End?

7.4 What Is the Structure & Chemistry of

Polysaccharides can form linear and branched structures

What Is the Storage Polysaccharide in Plants?

What Is the Storage Polysaccharide in Animals?

What Is the Most Common Structural Polysaccharide?

What Structural Polysaccharide Is Found in

What Are Glycosaminoglycans?

What Structural Polysaccharide Is Found in Bacterial Cell

What Is the Difference Between Gram-Positive Cell Walls

What Are the Structures of the Cell Wall & Membranes in

7.5 What Are Glycoproteins, & How Do They Function in

How Do Glycoproteins Interact With Membranes?

How Does Glycosylation Affect Proteins?

7.6 How Do Proteoglycans Modulate Processes in Cells?

What Are the Functions of Proteoglycans?

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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

Characteristic Chemical Features of Carbohydrates

Polysaccharides can form linear and branched structures