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CarbohydrateChemistryPart2:OtherCarbohydrates
Dr.KevinAhern
Nomenclature
Fischer Form Haworth Form
Disaccharides
• Sucrose(glucose+fructose)• Lactose(glucose+galactose)• Maltose(glucose+glucose)
Disaccharides• Comprised of two sugars
1
2
3 4
5
6
1
2
3
4
5
6
Sucrose
Glucose Fructose
α1, β2 Diglycosidic Links
α-D-glucopyranosyl-(1→2)-β-D-fructofuranoside
Sucrose
Fructose
1
2
34
5
6
Glucose 123
4
5
6
Disaccharides• Lactose and Maltose
Lactose Maltose
Glucose
Galactose
GlucoseGlucose
1
1
2
2
3
3
4
4
5
5
6
6
β-1,4 Glycosidic Bond
1 122
3 3
44
5 5
66
α-1,4 Glycosidic Bond
β-D-galactopyranosyl-(1→4)-D-glucose α-D-glucopyranosyl-(1→4)-D-glucose
ReducingVersusNon-ReducingSugars
Oligosaccharides
• Foundinglycoproteins• Playrolesincellularidentity
Polysaccharides
• Cellulose• Glycogen• Amylose• Amylopectin• Chitin
Glucose Glucose
Polysaccharides• Sugar Polymers With Glycosidic Bonds
Cellulose
β-1,4 Glycosidic Links
Polysaccharides• Sugar Polymers With Glycosidic Bonds
Glucose Glucose Glucose
Amylose - component of starch
α-1-4 Glycosidic Links
4 44 1 1 1
Amylose - component of starch
Polysaccharides
Amylopectin - component of starch
Glucose Glucose Glucose
GlucoseGlucose
α-1,4 Glycosidic Links
1 1 1444
α-1,6 Glycοsidic Link Branches
1 1
66
Polysaccharides
Polysaccharides• Sugar Polymers With Glycosidic Bonds
Glycogen
Glucose Glucose Glucose
GlucoseGlucose
α1,4 links
α1,6 links
ModifiedPolysaccharides
ChitinChitin in the wing of a sap beetle
ModifiedPolysaccharides
Pectin - gelling agent Galacturonic acid polymer α-1,4 bonds
PolysaccharidesBinding
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
Glycolipids• Glycoglycerolipids and Glycosphingolipids
Glycolipids• Glycoglycerolipids
Sugar
Diacylglycerol
Glycolipids• Glycosphingolipids
Cerebrosides
Single SugarSphingolipid Backbone
Glycolipids• Glycosphingolipids
Gangliosides
Sphingolipid Backbone
Complex Carbohydrate
Glycosaminoglycans-polyanionicpolymersofmodifiedsugarsProteoglycans-peptides/proteinslinkedtopolyanionicpolymersofmodifiedsugarsGlycoproteins-proteinslinkedtooligosaccharidesN-linked-joinedtoasparagineinprotein-E.R.andGolgiapparatusO-Linked-joinedtoserine/threonineinprotein-Golgiapparatus
Glycosylation
Glycosylation-glycoproteins
Glycosylation-Bloodtyping
Glycosaminoglycans• Unbranched polyanionic saccharide polymers
Chondroitin Sulfate
Heparin
MetabolicMelody
Structural Lullaby(To the tune of "Brahms' Lullaby")
Copyright © Kevin Ahern
In your sleepYou can keep
Learning more about sugarsFischer schemesHaworth rings
D & L and everything
HydroxidesCan’t collide
Fav’ring chair over boat formSpatial guides
CoincideWith the way structures form
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