Synthesis of a major mitomycin C DNA adduct via a triaminomitosene

Bioorg Med Chem Lett. 2012 Dec 1;22(23):7198-200. doi: 10.1016/j.bmcl.2012.09.052. Epub 2012 Sep 25.

Abstract

We report here the synthesis of two amino precursors for the production of mitomycin C and 10-decarbamoylmitomycin C DNA adducts with opposite stereochemistry at C-1. The triamino mitosene precursors were synthesized in 5 steps from mitomycin C. In addition synthesis of the major mitomycin C-DNA adduct has been accomplished via coupling of a triaminomitosene with 2-fluoro-O(6)-(2-p-nitrophenylethyl)deoxyinosine followed by deprotection at the N(2) and O(6) positions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • DNA Adducts / chemical synthesis
  • DNA Adducts / chemistry*
  • Isomerism
  • Mitomycin / chemical synthesis
  • Mitomycin / chemistry*
  • Mitomycins / chemistry*
  • Thermodynamics

Substances

  • DNA Adducts
  • Mitomycins
  • mitomycin C-DNA adduct
  • 10-decarbamoylmitomycin C
  • mitosene
  • Mitomycin