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Carbohydrates
Chapter 10, Stryer Short Course
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Basics of Carbs: Discussion Section
• Recognize and draw particular carbohydrate structures
• Know general structural elements of straight chain and cyclic monosaccharides
• Draw and name disaccharides• Understand structure/function relationships of
polysaccharides• Predict the products of glycoside formation and
breakdown
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Straight-chain Monosaccharides• Aldose/ketose terminology• Triose, tetrose, pentose, hexose• Stereochemistry: D, L designation– Fisher Projection
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Aldose Tree
Epimers
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Ketose Tree
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Structures to Know
• Dihydroxyacetone• D-glyceraldehyde• D-ribose• D-glucose• D-galactose• D-fructose• D-mannose
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Cyclic Monosaccharides
• Pyranose and furanose
• Haworth Projection
• Anomeric carbon• Alpha and beta
anomers
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Reducing Sugars
• Test for free aldehyde• Cyclic/acyclic equilibrium
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Conformations
• Haworth and chair commonly drawn• boats, envelopes, etc
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Summary of Terms
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Sugar Derivatives• Phosphate esters, aminosugars• Acylation
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Structure of Disaccharides
• Condensation of Monosacharides– Loss of anomeric hydroxyl group and proton of
nucleophilic alcohol– Glycosidic Bond
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Structure of Disaccharides
• Nomenclature of linkage– Find the acetal!– Number and linkage
• Reducing sugar– Find the hemiacetal!
• Identity of disaccharide based on sugars and linkage
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Lactose
• Lactose is a galactose unit with a b(14) linkage to glucose
• Milk sugar• Basis of lactose
intolerance: lactase• Notice the strange
glycosidic bond drawing convention
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Maltose
• Glucose linked through an a(14) linkage to another glucose
• Breakdown product of starch
• Maltase• Reducing sugar
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Sucrose
• Non-reducing sugar– No hemiacetal– Notice that fructose is
upside down
• Table sugar• Sucrase
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Glycosyltransferase
• Condensation is opposite of hydrolysis• Glycosidic bond formation catalyzed by many enzymes• Activated monosaccharide
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Polysaccharides
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Starch and Glycogen
Compact storage
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Cellulose
• Watch structure carefully!
Function: structural support
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Glycoproteins
• Many proteins are highly modified by addition of carbohydrates
• Structure and Recognition• N-linked—Asn• O-linked—Ser, Thr
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Modification of N-Linked Carbs
• Glycosyltransferases
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Blood types
• Genes for different glycosyltransferases
• Blood type: difference in antigen on surface of red blood cells
• Transfusions
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Congenital Disorders of Glycosylation
• Lysosyme digestive enzymes are marked for delivery by mannose-6-P
• A lectin (protein that selectively recognizes a glycan) on the lysozyme surface directs delivery
• If not phosphorylated, enzymes sent to wrong place
• Lysozymes cannot degrade glycosaminoglycan
• Buildup leads to skeletal and psychomotor retardation
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Glycoproteins
• Glycoproteins– Structural diversity– Many functions—based on recognition
• Proteoglycans– Bulk is carbohydrate– Linked to glucosaminoglycan– Structural, protective functions
• Mucoproteins– Lubricants, predominately carbs
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Example: Erythropoietin
• EPO-hormone• Glycoprotein• Recombinant
form used to treat anemia
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Proteoglycans
• Up to 95% carbs
• Cell adhesion• Highly
negatively charged
• Heparin: anticoagulant
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Example: Cartilage
• Shock absorber
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Peptidoglycan
• Bacterial cell wall• Target for penicillin
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Mucoproteins
• Variable number of tandem repeats
• Function to protect cells
• Overexpressed in cystic fibrosis