2.

Carbohydrate structures

BC5170 Integrated Structure Function

Donald Messner, PhD Summer 2023
Topics: learning objectives:

• monosaccharides
• classification of sugars and terms # 1a
• open chain chemical structures # 1b-1c
• closed ring chemical structures # 1d-1e

• carbohydrate (glycosidic) bonds:

• disaccharide structures # 1f-1g
• polysaccharide structures #2

• functions of carbohydrates #3

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(1) Carbohydrates are sugars (saccharides)
• basic formula: CnH2nOn (n=3 or more)

• "-ose"

• monosaccharides = ?

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Monosaccharide classification:

D-glucose is a ___________

(at least 2 different ways)

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 carbohydrate = sugar ≠ sweet

sweetness = 1:350:180

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Most carbohydrates in humans are D-isomers

5.10 D- vs L- sugars (p67)

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How are monosaccharides classified?

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5.11 common 6 carbon aldoses (p59)

D-glucose and 2 epimers 8

5.9 fructose is a common 6 carbon ketose (p66)

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Draw open chain structures for the D- forms of:

• C3: glyceraldehyde (aldose) and dihydroxyacetone (ketose)

• C4 and C5: erythrose and ribose, ribulose, xylulose

• C6: glucose, galactose, mannose, fructose

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Voet 8.1 D-aldoses

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Voet 8.2 D-ketoses

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What is an epimer?

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(1d) Monosacharides can be open chain or closed ring

open → closed
Left → Up
Right → Down

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(1e) 5.13 the anomeric carbon (C1 of glucose) in the ring can be a or b (p68)

mutarotation 15
Which carbon is the anomeric carbon?

What is mutarotation?

What is a pyranose?

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 17
Page 222
5.12 the closed ring form of fructose drawn as a
furanose, or five-membered ring (p68)

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Draw the a-furanose and the b-pyranose forms:

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recall the structure of ADP:

(find b-D-ribofuranose)

Glycosidic bonds link the anomeric carbon of carbohydrates

to other molecules
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 (1f) 5.16 N- and O- glycosidic bonds (p70).

glycosidic bonds are formed at the anomeric carbon by enzymes

(once that glycosidic bond is formed mutarotation cannot occur)

cleavage of glycosidic bonds also requires enzymes

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 gal C5

gal C1
’’
’’
gal C2 glu C4

glucose C4 galactose
anomeric C

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(1g) Disaccharides to know (lactose and sucrose):
(glucose a 1,2 fructose)

(galactose b 1,4 glucose)

Which of these can be either a or b (ie is a “reducing sugar)?

Be able to describe (sugars and bonds) and draw both.

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(2) 1.4 Polysaccharides; starch (p5)

In the gut, starch is digested by a-amylase, which cuts only glucose a1-4 glucose,
eg:

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 21.1 partial digestion of starch in the gut* results in (p416):

2 types of a-dextrins and 2 different disaccharides

H2COH H2COH
a linear OH OH
polymer of │ │ │ │
glucose OH OH

(glucose a 1,4 glucose)

H2COH

a branched
polymer of
glucose OH
│ │
OH

(glucose a 1,6 glucose)

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*(a-amylase cuts glucose a1-4 glucose)
 26.1 Polysacharides: glycogen (p525):

Glucose is harvested from glycogen in cells by the enzyme glycogen phosphorylase.

This enzyme chews glucose away one at a time from the non-reducing ends of glycogen.
Many available ends on glycogen allows this to go faster.
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Recall from last time (unit 1B, learning objective #9):

26.2 Liver and skeletal muscle have the highest levels of glycogen (p527)

The glycogen is used differently, however:

energy under anaerobic

(low oxygen) conditions

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Dietary fiber is polysaccharide that can’t be digested by human enzymes;
eg. cellulose is a glucose polymer with
• b 1,4 glycosidic bonds (not digestible in humans)
• no branch points (favors H-bonding to itself, not water)

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(3) Carbohydrate functions in humans
1. a source of energy (make ATP) that is stored as glycogen

2. an important building block for synthesizing other molecules

a) nucleotides, nucleic acids
b) glycoproteins and glycolipids

3. when attached to proteins and lipids, functions include:

a) blood type (molecular recognition)
b) extracellular matrix properties
c) sorting of lysosomal enzymes

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other molecules made from CHOs (a), e.g.

20.2 ribose is used to make ATP (p396)

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other molecules made from CHOs (b), e.g.

10.2 Proteins and lipids in the plasma membrane may contain CHOs (p154)

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Voet 8-21 electron micrograph of the glycocalyx (the carbohydrate coat)
on the surface of a Red Blood Cell.

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Molecular recognition;
(a) CHO on cell surface glycolipids determines blood type.

27.23 CHO structure → (p558)

type “O” ≡ core CHO structure only

type “A” ≡ blood cells contain an enzyme

that adds N-acetylgalactosamine

type “B” ≡ blood cells contain an enzyme

that adds galactose

type “AB” ≡ blood cells contain both enzymes

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Molecular recognition and function;
(b) CHOs on glycoproteins
47.11 proteins of the extracellular matrix (p988):

CHOs on glycoproteins in the

ECM provide:

-flexible structure; give cells

space to move within an organ

-filtration; small molecules

diffuse through CHOs, but large
molecules may not

- cell-cell and cell-ECM

recognition involves the CHO
portion of glycoproteins

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Molecular recognition;
(c) CHOs control the targeting of lysosomal enzymes

10.1 a eukaryotic cell (p170)

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sorting of newly synthesized lysosomal enzymes in the Golgi

default pathway for

membrane and mannose 6-P
targeted pathway 36
secreted proteins