Journal of Chemical Sciences

, Volume 120, Issue 1, pp 163–173

Propargyloxycarbonyl as a protecting group for the side chains of serine, threonine and tyrosine

  • Ramapanicker Ramesh
  • Kavita De
  • Shipra Gupta
  • Srinivasan Chandrasekaran
Article

DOI: 10.1007/s12039-008-0019-y

Cite this article as:
Ramesh, R., De, K., Gupta, S. et al. J Chem Sci (2008) 120: 163. doi:10.1007/s12039-008-0019-y

Abstract

Propargyloxycarbonyl group is used as a protecting group for the hydroxyl groups of serine, threonine and tyrosine. The propargyloxycarbonyl derivatives of these hydroxy amino acids are stable to acidic and basic reagents commonly employed in peptide synthesis. The deprotection of the O-Poc derivatives using tetrathiomolybdate does not affect commonly used protecting groups such as N-Boc, N-Cbz, N-Fmoc, methyl and benzyl esters. The di-and tripeptides synthesized using O-Poc derivatives of serine, threonine and tyrosine are stable, isolable compounds and give the hydroxy peptides in good yields when treated with tetrathiomolybdate.

Keywords

Protecting groupsamino acidspeptide synthesishydroxy residues

Copyright information

© Indian Academy of Sciences 2008

Authors and Affiliations

  • Ramapanicker Ramesh
    • 1
  • Kavita De
    • 1
  • Shipra Gupta
    • 1
  • Srinivasan Chandrasekaran
    • 1
    • 2
  1. 1.Department of Organic ChemistryIndian Institute of ScienceBangaloreIndia
  2. 2.Jawaharlal Nehru Centre for Advanced Scientific ResearchBangaloreIndia