Article

Journal of Chemical Sciences

, Volume 120, Issue 1, pp 163-173

First online:

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

  • Ramapanicker RameshAffiliated withDepartment of Organic Chemistry, Indian Institute of Science
  • , Kavita DeAffiliated withDepartment of Organic Chemistry, Indian Institute of Science
  • , Shipra GuptaAffiliated withDepartment of Organic Chemistry, Indian Institute of Science
  • , Srinivasan ChandrasekaranAffiliated withDepartment of Organic Chemistry, Indian Institute of ScienceJawaharlal Nehru Centre for Advanced Scientific Research Email author 

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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 groups amino acids peptide synthesis hydroxy residues