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Carbohydrate Structure

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Presentation on theme: "Carbohydrate Structure"— Presentation transcript:

1 Carbohydrate Structure
Biochemistry Free For All

2 Nomenclature Structures Cyclizations Modifications Outline
Simple Carbohydrates Nomenclature Structures Cyclizations Modifications

3 Saccharides X = Aldehydes = Aldoses Ketones = Ketoses Cx(H2O)x
Monosaccharides Cx(H2O)x Glucose (C6H12O6) Fructose (C6H12O6) Ribose (C5H10O5) Galactose (C6H12O6) Glyceraldehyde (C3H6O3) • Tri- = 3 • Tetr- = 4 • Pent- = 5 • Hex- =6 • Hept- = 7 • Oct- = 8 X = Aldehydes = Aldoses Ketones = Ketoses

4 Different Sizes 3 Carbons Triose 4 Carbons Tetrose 5 Carbons Pentose
The -oses 3 Carbons Triose 4 Carbons Tetrose 5 Carbons Pentose 6 Carbons Hexose D-Glyceraldehyde D-Threose D-Ribose D-Glucose

5 { } Aldose Ketose Common Sugars Aldehyde Ketone D-Glucose D-Fructose
Aldose and Ketose Aldehyde Ketone D-Glucose D-Fructose { } Aldose Ketose

6 Simple Sugars Aldopentose Aldohexose Ketohexose Aldohexose Aldohexose

7 Mirror Images L-Glyceraldehyde D-Glyceraldehyde Asymmetric Carbons
Penultimate Carbon The Glyceraldehydes D- Configuration L- Configuration Mirror Images L-Glyceraldehyde D-Glyceraldehyde

8 Multiple Asymmetric Centers
Glucose D-configuration Asymmetric Carbons D-Glucose

9 Enantiomers D-configuration L-configuration D-Glucose L-Glucose
Mirror Images D-configuration L-configuration D-Glucose L-Glucose

10 Diastereomers Same Configuration D-Glucose D-Gulose Different
Same chemical type & size, non-mirror images Same Configuration D-Glucose D-Gulose Different Configurations

11 Epimers D-Glucose D-Galactose
Diastereomers differing in configuration of one carbon only D-Glucose D-Galactose

12 The New Asymmetric Carbon
Cyclization of Sugars New Asymmetric Center In Close Spatial Proximity The New Asymmetric Carbon Is Called Anomeric

13 Cyclization of Sugars

14 Cyclization of Sugars

15 Haworth Structures Glucose Anomers α-D-Glucopyranose β-D-Glucopyranose

16 Common Furanoses β-D-Fructofuranose β-D-Ribofuranose
Fructose and Ribose β-D-Fructofuranose β-D-Ribofuranose

17 Conformational Isomers
Chair and Boat Forms of β-D-Glucose

18 Cyclic Structures Glucose

19 Fructose-1,6-bisphosphate
Modified Sugars Galactosamine N-acetylglucosamine Mannose-6-phosphate Fructose-1,6-bisphosphate Glucuronic Acid

20 Glycosides

21 Sugar Alcohol Sorbitol (Glucitol)

22 Artificial Sweeteners
Sucralose

23 Sucrose (glucose + fructose) Lactose (glucose + galactose)
Disaccharides Sucrose (glucose + fructose) Lactose (glucose + galactose) Maltose (glucose + glucose)

24 Polysaccharides Cellulose Glycogen Amylose Amylopectin Chitin

25 Hark the Sucrose (to the tune of "Hark the Herald") Copyright © Kevin Ahern
Metabolic Melody Carbohydrates all should sing Glory to the Haworth ring Anomeric carbons hide When they're in a glycoside Glucopyranose is there In the boat or in the chair Alpha, beta, D and L Di-astere-omer hell

26 Nomenclature Fischer Form Haworth Form

27 Sucrose (glucose + fructose) Lactose (glucose + galactose)
Disaccharides Sucrose (glucose + fructose) Lactose (glucose + galactose) Maltose (glucose + glucose)

28 Sucrose Sucrose Disaccharides Glucose α1, β2 Diglycosidic Links
Comprised of two sugars Sucrose Glucose 1 2 3 4 5 6 α1, β2 Diglycosidic Links 1 2 3 4 5 6 1 2 3 4 5 6 Fructose 1 2 3 4 5 6 Glucose Fructose Sucrose α-D-glucopyranosyl-(1→2)-β-D-fructofuranoside

29 Disaccharides Glucose Glucose Galactose α-1,4 Glycosidic Bond
Lactose and Maltose Glucose Galactose Glucose 1 2 3 4 5 6 β-1,4 Glycosidic Bond 1 2 3 4 5 6 α-1,4 Glycosidic Bond Lactose Maltose β-D-galactopyranosyl-(1→4)-D-glucose α-D-glucopyranosyl-(1→4)-D-glucose

30 Reducing Versus Non-Reducing Sugars

31 Found in glycoproteins Play roles in cellular identity
Oligosaccharides Found in glycoproteins Play roles in cellular identity

32 Polysaccharides Cellulose Glycogen Amylose Amylopectin Chitin

33 Cellulose Polysaccharides β-1,4 Glycosidic Links Glucose
Sugar Polymers With Glycosidic Bonds β-1,4 Glycosidic Links Glucose Cellulose

34 Amylose - component of starch
Polysaccharides Sugar Polymers With Glycosidic Bonds α-1-4 Glycosidic Links 4 1 Glucose Amylose - component of starch

35 Amylose - component of starch
Polysaccharides Amylose - component of starch

36 Amylopectin - component of starch
Polysaccharides α-1,6 Glycοsidic Link Branches 1 6 α-1,4 Glycosidic Links 1 4 Glucose Amylopectin - component of starch

37 Glycogen Polysaccharides α1,6 links α1,4 links Glucose
Sugar Polymers With Glycosidic Bonds α1,4 links Glucose Glycogen

38 Modified Polysaccharides
Chitin in the wing of a sap beetle Chitin

39 Modified Polysaccharides
Galacturonic acid polymer α-1,4 bonds Pectin - gelling agent

40 Polysaccharides Binding
Lectins - proteins that bind carbohydrates specifically Part of innate immune system Mannose binding lectin targets microbes Phytohemagglutinins in plants Used by bacteria/viruses for cellular attachment Tamiflu inhibits neuraminidase necessary for exit of flu virus

41 Glycolipids Glycoglycerolipids and Glycosphingolipids

42 Glycolipids Glycoglycerolipids Sugar Diacylglycerol

43 Sphingolipid Backbone
Glycolipids Glycosphingolipids Single Sugar Sphingolipid Backbone Cerebrosides

44 Sphingolipid Backbone
Glycolipids Complex Carbohydrate Glycosphingolipids Sphingolipid Backbone Gangliosides

45 Glycosylation Glycosaminoglycans - polyanionic polymers of modified sugars Peptidoglycans - peptides/proteins linked to polyanionic polymers of modified sugars Glycoproteins - proteins linked to oligosaccharides N-linked - joined to asparagine in protein - E.R. and Golgi apparatus O-Linked - joined to serine/threonine in protein - Golgi apparatus

46 Glycosylation - glycoproteins

47 Glycosylation - Blood typing

48

49

50 Chondroitin Sulfate Heparin
Glycosaminoglycans Unbranched polyanionic saccharide polymers Heparin

51 Structural Lullaby In your sleep You can keep
(To the tune of "Brahms' Lullaby") Copyright © Kevin Ahern Metabolic Melody In your sleep You can keep Learning more about sugars Fischer schemes Haworth rings D & L and everything Hydroxides Can’t collide Fav’ring chair over boat form Spatial guides Coincide With the way structures form

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