1361315-32-3Relevant academic research and scientific papers
Long-range intramolecular s → N acyl migration: A study of the formation of native peptide analogues via 13-, 15-, and 16-membered cyclic transition states
Ha, Khanh,Chahar, Mamta,Monbaliu, Jean-Christophe M.,Todadze, Ekaterina,Hansen, Finn K.,Oliferenko, Alexander A.,Ocampo, Charles E.,Leino, David,Lillicotch, Aaron,Stevens, Christian V.,Katritzky, Alan R.
, p. 2637 - 2648 (2012/06/04)
The intramolecular long-range S → N acyl migration via 13-, 15-, and 16-membered cyclic transition states to form native tetra- and pentapeptide analogues was studied on S-acylcysteine peptides containing β- or γ-amino acids. The pH-dependency study of the acyl migration via a 15-membered cyclic transition state indicated that the reaction is favored at a pH range from 7.0 to 7.6. Experimental observations are supported by structural and computational investigations.
S- to N-Acyl transfer in S-acylcysteine isopeptides via 9-, 10-, 12-, and 13-membered cyclic transition states
Bol'shakov, Oleg,Kovacs, Judit,Chahar, Mamta,Ha, Khanh,Khelashvili, Levan,Katritzky, Alan R.
, p. 704 - 709,6 (2012/12/12)
S-Acyl cysteine peptides containing α-, β- or γ-amino acid residues undergo long-range S- to N-acyl transfer to give analogs of native tripeptides and tetrapeptides containing additional carbon atoms in the chain. The ease of intramolecular S→N-acyl transfer relative to intermolecular transacylation is favored increasingly for 91213~10-membered cyclic transition states; the observed order is explained on conformational and intermolecular interaction considerations.
S- to N-Acyl transfer in S-acylcysteine isopeptides via 9-, 10-, 12-, and 13-membered cyclic transition states
Bol'shakov, Oleg,Kovacs, Judit,Chahar, Mamta,Ha, Khanh,Khelashvili, Levan,Katritzky, Alan R.
, p. 704 - 709 (2013/01/15)
S-Acyl cysteine peptides containing α-, β- or γ-amino acid residues undergo long-range S- to N-acyl transfer to give analogs of native tripeptides and tetrapeptides containing additional carbon atoms in the chain. The ease of intramolecular S→N-acyl transfer relative to intermolecular transacylation is favored increasingly for 91213~10-membered cyclic transition states; the observed order is explained on conformational and intermolecular interaction considerations.
