Solid-phase synthesis of succinylhydroxamate peptides: functionalized matrix metalloproteinase inhibitors

Org Lett. 2006 Apr 13;8(8):1705-8. doi: 10.1021/ol060409e.

Abstract

[reaction: see text] A novel solid-phase synthesis strategy toward succinylhydroxamate peptides, using an appropriately protected hydroxamate building block, is described. Rapid and efficient access is gained to amine-functionalized peptides, which can be decorated with, for instance, a fluorescent label. In addition, we demonstrate an on-resin synthesis of a biotinylated photoactivatable hydroxamate peptide, which can be used as an activity-based probe for matrix metalloproteinases and ADAMs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • ADAM Proteins / antagonists & inhibitors*
  • Enzyme Inhibitors / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Hydroxamic Acids / chemical synthesis*
  • Metalloendopeptidases / antagonists & inhibitors*
  • Molecular Structure
  • Peptides / chemical synthesis*
  • Succinates / chemical synthesis*

Substances

  • Enzyme Inhibitors
  • Fluorescent Dyes
  • Hydroxamic Acids
  • Peptides
  • Succinates
  • ADAM Proteins
  • Metalloendopeptidases