title: 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.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
authors.forename: Stephen
authors.initials: S
authors.lastname: Chamberland
authors.forename: Sabine
authors.initials: S
authors.lastname: Grüschow
authors.forename: David H
authors.initials: DH
authors.lastname: Sherman
authors.forename: Robert M
authors.initials: RM
authors.lastname: Williams
mesh_terms: D000903:Antibiotics, Antineoplastic / Q000096:biosynthesis* / Q000737:chemistry / Q000494:pharmacology; D016685:Mitomycin / Q000096:biosynthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
chemical_list: D000903:Antibiotics, Antineoplastic; D010078:Oxazines; C053335:FR 900482; D016685:Mitomycin