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Synthesis of potential early-stage intermediates in the biosynthesis of FR900482 and mitomycin C.

ABSTRACT: Beyond the identification of 3-amino-5-hydroxybenzoic acid (AHBA) and D-glucosamine as biosynthetic precursors to mitomycin C (5) and FR900482 (6), little is known about the pathway Nature uses to prepare these antitumor antibiotics. To gain some insight into their biosynthesis, amino acids 1 and 2 as well as C-2 N-acetylated derivatives 3 and 4 were prepared. Preparation of these putative biosynthetic intermediates and N-acetylcysteamine thioester analogues 28 and 29 should enable confirmation of their involvement in FR900482 and mitomycin C biosynthesis.

SUBMITTER: Chamberland S

PROVIDER: S-EPMC2647965 | biostudies-literature | 2009 Feb

REPOSITORIES: biostudies-literature

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Synthesis of potential early-stage intermediates in the biosynthesis of FR900482 and mitomycin C.

Chamberland Stephen S Grüschow Sabine S Sherman David H DH Williams Robert M RM

Organic letters 20090201 4

Beyond the identification of 3-amino-5-hydroxybenzoic acid (AHBA) and D-glucosamine as biosynthetic precursors to mitomycin C (5) and FR900482 (6), little is known about the pathway Nature uses to prepare these antitumor antibiotics. To gain some insight into their biosynthesis, amino acids 1 and 2 as well as C-2 N-acetylated derivatives 3 and 4 were prepared. Preparation of these putative biosynthetic intermediates and N-acetylcysteamine thioester analogues 28 and 29 should enable confirmation ...[more]

PMID: 19161340

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