One-pot peptide ligation-desulfurization at glutamate

Org Lett. 2014 Jan 3;16(1):290-3. doi: 10.1021/ol403288n. Epub 2013 Dec 2.

Abstract

An efficient methodology for ligation at glutamate (Glu) is described. A γ-thiol-Glu building block was accessed in only three steps from protected glutamic acid and could be incorporated at the N-terminus of peptides. The application of these peptides in one-pot ligation-desulfurization chemistry is demonstrated with a range of peptide thioesters, and the utility of this methodology is highlighted through the synthesis of the osteoporosis peptide drug teriparatide (Forteo).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glutamic Acid / chemistry*
  • Molecular Structure
  • Peptides / chemical synthesis*
  • Peptides / chemistry*
  • Teriparatide / chemical synthesis*
  • Teriparatide / chemistry

Substances

  • Peptides
  • Teriparatide
  • Glutamic Acid