Synthesis of potential early-stage intermediates in the biosynthesis of FR900482 and mitomycin C.
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.
Chamberland
Stephen
S
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Grüschow
Sabine
S
Sherman
David H
DH
Williams
Robert M
RM
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
D000903:Antibiotics, Antineoplastic; D010078:Oxazines; C053335:FR 900482; D016685:Mitomycin