MIT 5 451 - Problem Set 3 (4 pages)

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Problem Set 3



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Problem Set 3

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Pages:
4
School:
Massachusetts Institute of Technology
Course:
5 451 - Chemistry of Biomolecules I
Chemistry of Biomolecules I Documents

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5 451 F2005 Problem Set 3 1 25 pts Using your knowledge of the 20 proteogenic amino acids propose the starting material as well as a mechanism of biosynthesis for the following alkaloid General acid bases catalysis and an oxygenase reaction is utilized H H N OH NH2 HN N H H Professor Sarah O Connor Massachusetts Institute of Technology OH O 5 451 F2005 Problem Set 3 2 25 pts Propose 3 naturally occuring starting materials and a mechanism using general acid base catalysis for assembling them to yield the following alkaloid O NH H HN O N H Professor Sarah O Connor Massachusetts Institute of Technology 5 451 F2005 Problem Set 3 3 25 pts A E Monoterpene biosynthesis Draw the mechanism of biosynthesis for each of the following monoterpenes starting from geranyl diphosphate Include all intermediates and utilize arrows to indicate the flow of electrons These reactions are enzymatically catalyzed by a terpene cyclase so utilize general acid base catalysis A B C D E OH Professor Sarah O Connor Massachusetts Institute of Technology 5 451 F2005 Problem Set 3 4 25 pts Sesquiterpene biosynthesis Propose a detailed mechanism of biosynthesis from farnesyl diphosphate for the following unusual sesquiterpene The last step that converts the intermediate to the final product is not typically observed in terpene biosynthesis farnesyl diphosphate terpene cyclase Professor Sarah O Connor Massachusetts Institute of Technology intermediate



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