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Long‐Range Chemical Ligation from N→N Acyl Migrations in Tryptophan Peptides via Cyclic Transition States of 10‐ to 18‐Members
Author(s) -
Biswas Suvendu,
Kayaleh Roger,
Pillai Girinath G.,
Seon Christopher,
Roberts Ian,
Popov Vadim,
Alamry Khalid A.,
Katritzky Alan R.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201400125
Subject(s) - native chemical ligation , intramolecular force , chemistry , ligation , chemical ligation , tryptophan , peptide , stereochemistry , combinatorial chemistry , chemical synthesis , in vitro , amino acid , biochemistry , biology , microbiology and biotechnology
Chemical ligations to form native peptides from N→N acyl migrations in Trp‐containing peptides via 10‐ to 18‐membered cyclic transition states are described. In this study, a statistical, predictive model that uses an extensive synthetic and computational approach to rationalize the chemical ligation is reported. N→N acyl migrations that form longer native peptides without the use of Cys/Ser/Tyr residues or an auxiliary group at the ligation site were achieved. The feasibility of these traceless chemical ligations is supported by the NC bond distance in N ‐acyl isopeptides. The intramolecular nature of the chemical ligations is justified by using competitive experiments and theoretical calculations.