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

Ramesh, Ramapanicker and De, Kavita and Gupta, Shipra and Chandrasekaran, Srinivasan (2008) Propargyloxycarbonyl as a protecting group for the side chains of serine, threonine and tyrosine. In: Proceedings of the Indian Academy of Sciences - Chemical Sciences, 120 (1). pp. 163-173.

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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.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Indian Academy of Sciences.
Keywords: Protecting groups;amino acids;peptide synthesis;hydroxy residues.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 30 Mar 2010 07:38
Last Modified: 19 Sep 2010 05:58
URI: http://eprints.iisc.ernet.in/id/eprint/26682

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