Selective Peptide Chain Extension at the N-terminus of Aspartic and Glutamic Acids Utilizing 1-(N-protected-α-aminoacyl)benzotriazoles

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‐α‐aminoacyl)benzotriazoles of the amino groups of free aspartic and glutamic acids. Complete retention of c...

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Veröffentlicht in:	Chemical biology & drug design 2006-07, Vol.68 (1), p.37-41
Hauptverfasser:	Katritzky, Alan R., Todadze, Ekaterina, Cusido, Janet, Angrish, Parul, Shestopalov, Alexander A.
Format:	Artikel
Sprache:	eng
Schlagworte:	Aminoacylation aspartic acid Aspartic Acid - chemical synthesis Aspartic Acid - chemistry benzotriazole methodology Chromatography, High Pressure Liquid glutamic acid Glutamic Acid - chemical synthesis Glutamic Acid - chemistry Magnetic Resonance Spectroscopy N-protected(α-aminoacyl)benzotriazole Oligopeptides - chemical synthesis Oligopeptides - chemistry small peptides Stereoisomerism Triazoles - chemical synthesis Triazoles - chemistry
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description	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‐α‐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.
doi_str_mv	10.1111/j.1747-0285.2006.00411.x
format	Article
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subjects	Aminoacylation aspartic acid Aspartic Acid - chemical synthesis Aspartic Acid - chemistry benzotriazole methodology Chromatography, High Pressure Liquid glutamic acid Glutamic Acid - chemical synthesis Glutamic Acid - chemistry Magnetic Resonance Spectroscopy N-protected(α-aminoacyl)benzotriazole Oligopeptides - chemical synthesis Oligopeptides - chemistry small peptides Stereoisomerism Triazoles - chemical synthesis Triazoles - chemistry
title	Selective Peptide Chain Extension at the N-terminus of Aspartic and Glutamic Acids Utilizing 1-(N-protected-α-aminoacyl)benzotriazoles
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