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Biochemical Reaction Mechanisms 1. Mechanism of action of -chymotrypsin 2. Glycolysis: metabolism of glucose 3. Biosynthesis of steroids from squalene
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Mechanism of action of -chymotrypsin (An enzyme that hydrolyzes peptides in the digestive system)
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Catalytic triad: Asp 102, His 57, Ser 195
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-chymotrypsin mechanism…
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Glycolysis Metabolism of glucose to form pyruvate and ATP
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Glycolysis converts glucose into two pyruvate molecules ä …with the production of 2 ATPs (high energy storage in cells) 1. Isomerization of glucose to fructose 2. Formation of iminium ion; retro aldol to form two 3-carbon sugars (as phosphates) 3. Isomerization of dihydroxyacetone to glyceraldehyde (as phosphates) 4. Oxidation, isomerization, dehydration and dephosphorylation to form pyruvate and ATP
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Isomerization of glucose to fructose
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Iminium ion; retro aldol addition
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Isomerization to glyceraldehyde
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Oxidation, isomerization and dephosphorylation (ATP forming)
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Biosynthesis of Steroids from Squalene
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Squalene (a shark oil terpene)
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Epoxidation of Squalene
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Acid-Catalyzed Epoxide Ring Opening; A Ring Formation A
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Reaction of Alkene with Carbocation; B Ring A BA
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Cyclization to form C Ring B C A A B
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Cyclization to form D Ring D C AB
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Hydride and Methyl Shifts
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Eventually...Cholesterol !
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Grading / Final Exam You may replace any of the 5 tests by an improved grade on that section of the Exam. Only the higher grade counts. You need not retake a section if you are happy with your grade on that test. Everyone must take Section 6 (Ch 25, 26, 27 & 29) plus Section 7 (comprehensive; mostly synthesis) Example: Your (best) score on these seven sections plus the sum of your gla scores determines your grade.
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