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

Journal of Chemical Sciences

Kavita De²  Ramapanicker Ramesh²  Shipra Gupta²  Srinivasan Chandrasekaran¹ 

[1] Jawaharlal Nehru Centre for Advanced Scientific Research, Bangalore 560 064$$;Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012$$

关键词: Protecting groups;    amino acids;    peptide synthesis;    hydroxy residues.;   

DOI  :  

来源: Indian Academy of Sciences

【 摘 要 】

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.

【 授权许可】

Unknown