Stereochemical Preference in the Reactions of N-Protected L-Amino Acid 1-Hydroxybenzotriazole Esters with Racemic Amino Acid Derivatives

Authors: Miyazawa, Toshifumi; Ozawa, Ayako; Furuhashi, Motohiro; Munegumi, Toratane

Source: Protein and Peptide Letters, Volume 16, Number 3, March 2009 , pp. 297-300(4)

Publisher: Bentham Science Publishers

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Abstract:

Stereochemical preference for homochiral or heterochiral couplings was investigated in the reactions of Nprotected L-amino acid 1-hydroxybenzotriazole esters with racemic amino acid derivatives. It was found to be dependent on the combination of amino acid residues as the carboxyl and amino components and the protecting groups of the amino acid residues, especially the N-protecting groups. Very high diastereomeric ratios were observed when t-leucine was employed as the carboxyl component and/or proline as the amino component and when the N-protecting group was the phthaloyl group.

Keywords: Stereochemical preference; competitive peptide synthesis; diastereomeric ratio; heterochiral coupling; homochiral coupling

Document Type: Research article

DOI: http://dx.doi.org/10.2174/092986609787601723

Publication date: 2009-03-01

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Protein & Peptide Letters publishes short papers in all important aspects of protein and peptide research, including structural studies, recombinant expression, function, synthesis, enzymology, immunology, molecular modeling, drug design etc. Manuscripts must have a significant element of novelty, timeliness and urgency that merit rapid publication. Reports of crystallisation, and preliminary structure determinations of biologically important proteins are acceptable. Purely theoretical papers are also acceptable provided they provide new insight into the principles of protein/peptide structure and function.