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Selective peptide chain extension at the N-terminus of aspartic and glutamic acids utilizing 1-(N-protected-alpha-aminoacyl)benzotriazoles
Journal article   Peer reviewed

Selective peptide chain extension at the N-terminus of aspartic and glutamic acids utilizing 1-(N-protected-alpha-aminoacyl)benzotriazoles

Alan R Katritzky, Ekaterina Todadze, Janet Cusido, Parul Angrish and Alexander A Shestopalov
Chemical biology & drug design, Vol.68(1), pp.37-41
07/2006
DOI: https://doi.org/10.1111/j.1747-0285.2006.00411.x
PMID: 16923024

Abstract

Aminoacylation Aspartic Acid - chemical synthesis Aspartic Acid - chemistry Chromatography, High Pressure Liquid Glutamic Acid - chemical synthesis Glutamic Acid - chemistry Magnetic Resonance Spectroscopy Oligopeptides - chemical synthesis Oligopeptides - chemistry Stereoisomerism Triazoles - chemical synthesis Triazoles - chemistry
Diverse N-protected di-(3a-d, 3a + a', 5a-d, 5d + d', and 7a-g) and tripeptides (10a-h) were synthesized under mild reaction conditions in good yields (65-97%) by acylation with 1-(N-protected-alpha-aminoacyl)benzotriazoles of the amino groups of free aspartic and glutamic acids. Complete retention of chirality was demonstrated by parallel experiments involving D-Ala, L-Ala, and DL-Ala for the preparation of dipeptides and tripeptides, and supported by NMR and HPLC analyses.

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