An alpha-formylglycine building block for fmoc-based solid-phase peptide synthesis

Org Lett. 2006 Jan 5;8(1):131-4. doi: 10.1021/ol052623t.

Abstract

[reaction: see text] Nearly all known sulfatases share a common active site modification that is required for their activity: conversion of cysteine to alpha-formylglycine. We report the synthesis of an alpha-formylglycine building block suitable for Fmoc-based solid-phase peptide synthesis. The building block was incorporated into a synthetic peptide derived from the active site of a Mycobacterium tuberculosis sulfatase.

Publication types

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

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / chemistry
  • Binding Sites
  • Glycine / analogs & derivatives*
  • Glycine / chemistry
  • Mycobacterium tuberculosis / enzymology
  • Peptides / chemical synthesis*
  • Sulfatases / chemistry
  • Sulfatases / metabolism

Substances

  • Peptides
  • C(alpha)-formylglycine
  • Sulfatases
  • Alanine
  • Glycine