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Benzotriazole-Mediated Synthesis of Aza-peptides: En Route to an Aza-Leuenkephalin Analogue
Faculty
Pharmacy
Year:
2013
Type of Publication:
Article
Pages:
3541-3552
Authors:
Abo-Dya, Nader E, Katritzky, Alan R, Biswas, Suvendu, Avan, Ilker, Basak, Akash, Alamry, Khalid A
DOI:
10.1021/jo302251e
Journal:
JOURNAL OF ORGANIC CHEMISTRY AMER CHEMICAL SOC
Volume:
78
Research Area:
Chemistry
ISSN
ISI:000319708300031
Keywords :
Benzotriazole-Mediated Synthesis , Aza-peptides: , Route , , Aza-Leuenkephalin Analogue
Abstract:
Novel N-(N-Pg-azadipeptidoyl)benzotriazoles 20a-e couple efficiently with alpha-amino acids 21a-e, dipeptides 22a-c, aminoxyacetic acid 23a, depsidipeptide 23b, and alpha-hydroxy-beta-phenylpropionic acid 27 yielding, respectively, azatripeptides 24a-g, azatetrapeptides 25a,b, a hybrid azatripeptide with an oxyamide bond 26a, a hybrid azatetrapeptide with an ester bond 26b, and a hybrid azatripeptide with an ester bond 28. A new protocol for the synthesis of N-Pg-azatripeptides 33a,b and 35a,b, each containing a natural amino acid at the N-terminus, avoids the low coupling rates of the aza-amino acid residue and enables the solution-phase synthesis of an azaphenylalanine analogue of Leu-enkephalin 40.
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