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- Title
Long-Range Chemical Ligation from N→N Acyl Migrations in Tryptophan Peptides via Cyclic Transition States of 10- to 18-Members.
- Authors
Biswas, Suvendu; Kayaleh, Roger; Pillai, Girinath G.; Seon, Christopher; Roberts, Ian; Popov, Vadim; Alamry, Khalid A.; Katritzky, Alan R.
- Abstract
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.
- Subjects
PEPTIDES; CHEMICAL synthesis; ISOPEPTIDE bonds; INTRAMOLECULAR catalysis; CHEMICAL reactions
- Publication
Chemistry - A European Journal, 2014, Vol 20, Issue 26, p8189
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201400125