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

Org Lett. 2009 Feb 19;11(4):791-4. doi: 10.1021/ol802631c.

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.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Antibiotics, Antineoplastic / biosynthesis*
  • Antibiotics, Antineoplastic / chemistry
  • Antibiotics, Antineoplastic / pharmacology
  • Mitomycin / biosynthesis*
  • Mitomycin / chemistry
  • Mitomycin / pharmacology
  • Molecular Structure
  • Oxazines / chemical synthesis
  • Oxazines / chemistry
  • Oxazines / pharmacology
  • Stereoisomerism
  • Streptomyces / chemistry

Substances

  • Antibiotics, Antineoplastic
  • Oxazines
  • FR 900482
  • Mitomycin