Biochemical Reaction Mechanisms 1. Mechanism of action of  -chymotrypsin 2. Glycolysis: metabolism of glucose 3. Biosynthesis of steroids from squalene.

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Presentation transcript:

Biochemical Reaction Mechanisms 1. Mechanism of action of  -chymotrypsin 2. Glycolysis: metabolism of glucose 3. Biosynthesis of steroids from squalene

Mechanism of action of  -chymotrypsin (An enzyme that hydrolyzes peptides in the digestive system)

Catalytic triad: Asp 102, His 57, Ser 195

 -chymotrypsin mechanism…

Glycolysis Metabolism of glucose to form pyruvate and ATP

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

Isomerization of glucose to fructose

Iminium ion; retro aldol addition

Isomerization to glyceraldehyde

Oxidation, isomerization and dephosphorylation (ATP forming)

Biosynthesis of Steroids from Squalene

Squalene (a shark oil terpene)

Epoxidation of Squalene

Acid-Catalyzed Epoxide Ring Opening; A Ring Formation A

Reaction of Alkene with Carbocation; B Ring A BA

Cyclization to form C Ring B C A A B

Cyclization to form D Ring D C AB

Hydride and Methyl Shifts

Eventually...Cholesterol !

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.