MIT 5 451 - Problem Set 1 -5.451 (5 pages)

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Problem Set 1 -5.451



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Problem Set 1 -5.451

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Pages:
5
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 1 1 25 pts Shown below is the structure of the cyclic peptide cystothiazole a potent antibiotic produced by the bacteria Cystobacter fuscus Draw a reasonable biosynthetic pathway that includes chemical structures of intermediates and the names or abbreviation of the types of enzymes involved OCH3 S N N S O H3CO cystothiazole Professor Sarah O Connor Massachusetts Institute of Technology OCH3 5 451 F2005 Problem Set 1 2 25 pts Predict the structure of the polyketide that is encoded by the following set of enzymes KS Q AT mm ACP KS AT mm KR ACP KS AT m DH KR ACP enzyme 1 KS AT mm ACP KS AT mm DH ER KR ACP enzyme 2 KS AT mm enzyme 3 Professor Sarah O Connor Massachusetts Institute of Technology KR ACP KS AT mm ACP TE 5 451 F2005 Problem Set 1 3 20 pts Labeling studies have shown that the following molecule from Streptomyces coelicolor is made up of one unit of proline one unit of serine one unit of glycine and multiple units of acetate i e malonyl CoA The biosynthetic pathway is convergent with the two intermediates A and B condensing to form the final product Propose biosynthetic pathways for A and B and indicate the basic type of enzymes that would be used for the biosynthetic steps acetate glycine A NH NH H3CO proline serine acetate SAM note a PLP enzyme decarboxylates serine in this pathway H N HN Professor Sarah O Connor Massachusetts Institute of Technology N O H3CO B HN 5 451 F2005 Problem Set 1 4 20 pts Draw the thioester tethered linear polyketide intermediate for the following compound and show the steps that convert the intermediate into the final product Enzymes not required to be mentioned in the answer If the producing organism Streptomyces glaucescens is cultured in the presence of 1 2 13C2 acetate show the 13C labeling pattern expected to be observed in the final product using a bold line between the desired two carbons example HO OH O OH O OH Professor Sarah O Connor Massachusetts Institute of Technology 5 451 F2005 Problem Set



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