395GLec17_09 - Some Key Chemistry Concepts A brief summary...

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Some Key Chemistry Concepts A brief summary of vitamins and cofactors A brief interlude on digestion Metabolic pathways Ta daa…. .glycolysis
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Fig. 16-5a Biologically important nucleophilic and electrophilic groups. ( a ) Nucleophiles. Page 553
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Fig. 16-5b Biologically important nucleophilic and electrophilic groups. ( b ) Electrophiles. Page 553
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Four categories of biochemical reactions (according to Voet): Group-transfer reactions Redox reactions Elimination / Isomerization / Rearrangement reactions Making or Breaking - C- C - bonds
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Page 554
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Fig. 16-7 The phosphoryl- transfer reaction catalyzed by hexokinase. Page 555
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Fig. 16-8 The molecular formula and redox reactions of the coenzyme flavin adenine dinucleotide (FAD). Page 556
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Elimination, isomerization, rearrangement Eliminations create double bonds; multiple mechanisms may be used. Isomerization involves INTRAmolecular hydrogen shifts. Rearrangements produced an altered CARBON skeleton.
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Recall: pKa for CH 4 =58 pKa for CH 3 COCH 3 = 20
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Schiff base (imine) formation
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Cofactors and coenzymes Many proteins, including enzymes, function with only amino acid side chains; chymotrypsin is an example. Some proteins require non-protein groups for proper structure or function. These groups are referred to as “prosthetic groups”; they may include glycosylations, lipids, metals, and more. Enzymes may also require a non-protein group for activity; these are often called cofactors. Some enzyme cofactors may be metals, like Zn ++ or Cu ++ , but others may be larger, organic compounds. These groups can participate in chemistry that is not available to the side chains of the amino acids . Many times these cofactors are derived from vitamins. (Most vitamins must be ingested, we have lost the ability to synthesize them). Some organic cofactors stay bound to an enzyme, and although they may be altered during reaction, they must be “rejuvenated” in situ. Flavins are like this. Some vitamin derived cofactors turn over, like a substrate, with each reaction, and diffuse away. NAD/NADH is like this. These are sometimes called cosubstrates or coenzymes.
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Some Vitamins and Cofactors Know this for the test Decarboxylation
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A few vitamin structures The vitamin is generally added to a “marker” group or a chemical “handle” to form a cofactor.
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Some cofactor/coenzymes
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Some more cofactors
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Formal Oxidation States Formal oxidation state (FOS) analysis is useful in examining redox reactions. Recall these rules from General Chem 1. C-C bonds are shared equally
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395GLec17_09 - Some Key Chemistry Concepts A brief summary...

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