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Selective Peptide Chain Extension at the N‐terminus of Aspartic and Glutamic Acids Utilizing 1‐( N ‐protected‐ α ‐aminoacyl)benzotriazoles
Author(s) -
Katritzky Alan R.,
Todadze Ekaterina,
Cusido Janet,
Angrish Parul,
Shestopalov Alexander A.
Publication year - 2006
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/j.1747-0285.2006.00411.x
Subject(s) - chemistry , peptide , aspartic acid , chain (unit) , glutamic acid , stereochemistry , extension (predicate logic) , combinatorial chemistry , amino acid , biochemistry , computer science , physics , astronomy , programming language
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.