May 21 st, 2008 Biochemistry Recitation
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1 May 21 st, 2008 Biochemistry Recitation MBioS 303 Summer 2008 Outline Carbohydrate basics Aldoses vs. ketoses L and D configurations and anomers Glycosidic bonds, disaccharides Polysaccharides Storage: amylose and amylopectin (glycogen, starch) Structural: cellulose, chitin Nucleotide structure (esp. ATP) NAD(P), FAD 1
2 Carbohydrate Basics Types of Carbohydrates Aldoses vs. Ketoses Aldose sugars have an aldehyde group at the C1 position Biochemistry, 5 th Ed. 2
3 Types of Carbohydrates Aldoses vs. Ketoses Ketose sugars have a ketone group at the C2 position Biochemistry, 5 th Ed. Carbohydrate Stereochemistry Sugars can be in L or D configuration Classified based on the chiral carbon farthest from carbonyl group L or D designation referenced to that in glyceraldehyde If the hydroxyl group at the farthest chiral carbon is on the left side in the Fischer projection, the sugar is in the L configuration If the hydroxyl group at the farthest chiral carbon is on the right side in the Fischer projection, the sugar is in the D configuration 3
4 Carbohydrate Stereochemistry CHO CHO What is the carbon numbering sy stem? OH HO CH 2 OH CH 2 OH D-Glucose L-Glucose Carbohydrate Ring Formation (1) What ty pe of sugar is glucose an aldose or a ketose? (2) When f orming a ring structure, what hy droxy l group acts as the nucleophile, and what carbon does it attack? How do y ou know what side of the ring the substituents will be on? 4
5 Anomeric Carbons How do y ou distinguish the α-anomer f rom the β-anomer? Glycosidic Bonds O-glycosidic bond: formed when hydroxyl on one sugar reacts with anomeric carbon on another sugar O-gly cosidic bond 5
6 Glycosidic Bonds: Disaccharides What is unique about the structure of fructose? Polysaccharides Polymers of monosaccharides Linked by glycosidic bonds 6
7 Amylose: A Storage Polysaccharide Amylose: Unbranched polymer of glucose monosaccharides α1 4 linkages One component of starch in plants Amylose: A Storage Polysaccharide Amylose: Unbranched polymer of glucose monosaccharides α1 4 linkages One component of starch in plants α1 4 linkages cause bending resulting in overall helical structure 7
8 Amylopectin: A Storage Polysaccharide Amylopectin: Branched polymer of glucose monosaccharides Branching approximately every residues α1 4 linkages within one strand, α1 6 branch points Second component of starch in plants Why might branching be usef ul? Glycogen: A Storage Polysaccharide Similar to amylopectin Branched polymer of glucose monosaccharides Branching approximately every 8-12 residues α1 4 linkages within one strand, α1 6 branch points Energy storage in animals (mainly in liver cells) 8
9 Amylopection versus Glycogen The Cell: A Molecular Approach, 2 nd Ed. Cellulose: A Structural Polysaccharide Unbranched polymer of glucose monosaccharides Found in plant cell walls β1 4 linkages Neighboring monosaccharides flipped 180⁰ relative to each other Water insoluble why?? What ef fect do the β1 4 gly cosidic bonds hav e on the structure of cellulose? 9
10 Cellulose: A Structural Polysaccharide Forms sheets Stabilized by (1) hydrogen bonds, and (2) van derwaals interactions Cellulose: A Structural Polysaccharide Most organisms cannot digest cellulose No enzyme to break the β1 4 glycosidic bonds This is what our dietary fiber is made up of 10
11 Storage vs. Structural Polysaccharides The Cell: A Molecular Approach, 2 nd Ed. Chitin: A Structural Polysaccharide Unbranched polymer of N-acetyl-D-glucosamine monomers Found in many insect and arthropod exoskeletons, fungi cell walls, etc. β1 4 linkages Confer properties similar to those of cellulose 11
12 Nucleotides Nucleotides 12
13 Pyrimidines and Purines How can you remember which is a purine and which is a pyrimidine? Pyrimidines and Purines 13
14 Pyrimidines and Purines ATP ADENINE N-gly cosidic bond PHOSPHATES RIBOSE 14
15 Electron Carriers NAD(P) +, FAD NAD(P) + and FAD are electron carriers Can donate or accept electrons, depending on their oxidation state This means they undergo redox reactions! Electron donors can give electrons away, electron acceptors can accept additional electrons Notation is important!! NAD(P) + and FAD: they are in the oxidized state (can accept electrons) NAD(P)H and FADH 2 are indicating that they are in the reduced state (can donate electrons) 15
16 NAD +, NADH NIACIN Deficiency leads to Pellagra FAD, FADH 2 RIBOFLAVIN 16
17 QUIZ TIME! 17
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