Solid-phase synthesis of oligourea peptidomimetics employing the Fmoc protection strategy

J Org Chem. 2001 Dec 14;66(25):8454-62. doi: 10.1021/jo010656q.

Abstract

A solid-phase-Fmoc-based-synthesis strategy is described for oligourea peptidomimetics as well as a convenient general synthesis approach for the preparation of the required building blocks 5a-j and 5k. These are suitable for use in peptide or robot synthesizers, which is illustrated by the synthesis of oligourea peptidomimetics of part of Leu-enkephalin (10) and a neurotensin derivative (17).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry
  • Amino Alcohols / chemistry
  • Chromatography, High Pressure Liquid
  • Enkephalin, Leucine / analogs & derivatives
  • Enkephalin, Leucine / chemical synthesis
  • Fluorenes / chemistry*
  • Indicators and Reagents
  • Molecular Mimicry
  • Neurotensin / analogs & derivatives
  • Neurotensin / chemical synthesis
  • Oligopeptides / chemical synthesis*
  • Polymers
  • Urea / analogs & derivatives*
  • Urea / chemical synthesis*
  • Urea / chemistry

Substances

  • Amino Acids
  • Amino Alcohols
  • Fluorenes
  • Indicators and Reagents
  • Oligopeptides
  • Polymers
  • Neurotensin
  • Enkephalin, Leucine
  • Urea
  • 1-(9-fluorenyl)methyl chloroformate