Total synthesis of proximicin A-C and synthesis of new furan-based DNA binding agents

Org Lett. 2009 Jul 2;11(13):2804-7. doi: 10.1021/ol901003p.

Abstract

The total synthesis of the natural occurring polyamides proximicin A-C (3-5) has been accomplished. A short and efficient synthesis of a thus far unknown 4-amino-2-furan carboxylic acid was developed. Furthermore, this unique heterocyclic gamma-amino-acid was used for the synthesis of a new class of AT-selective DNA-binding agents derived from the natural products combining structural features of the proximicins with those from the known DNA-binding natural products netropsin (1) and distamycin (2).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis
  • Amino Acids / chemistry
  • DNA / chemistry*
  • DNA / metabolism
  • Distamycins / chemistry
  • Distamycins / pharmacology
  • Furans / chemistry*
  • Molecular Structure
  • Netropsin / analogs & derivatives*
  • Netropsin / chemical synthesis
  • Netropsin / chemistry
  • Netropsin / pharmacology
  • Nylons / chemical synthesis*
  • Nylons / chemistry

Substances

  • Amino Acids
  • Distamycins
  • Furans
  • Nylons
  • proximicin A
  • proximicin B
  • proximicin C
  • Netropsin
  • stallimycin
  • DNA
  • furan