Sugar-derived oxazolone pseudotetrapeptide as γ-turn inducer and anion-selective transporter

Autor: Sachin S. Burade, Sushil V. Pawar, Tanmoy Saha, Navanath Kumbhar, Amol S. Kotmale, Manzoor Ahmad, Pinaki Talukdar, Dilip D. Dhavale
Jazyk: angličtina
Rok vydání: 2019
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 15, Iss 1, Pp 2419-2427 (2019)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.15.234
Popis: The intramolecular cyclization of a C-3-tetrasubstituted furanoid sugar amino acid-derived linear tetrapeptide afforded an oxazolone pseudo-peptide with the formation of an oxazole ring at the C-terminus. A conformational study of the oxazolone pseudo-peptide showed intramolecular C=O···HN(II) hydrogen bonding in a seven-membered ring leading to a γ-turn conformation. This fact was supported by a solution-state NMR and molecular modeling studies. The oxazolone pseudotetrapeptide was found to be a better Cl−-selective transporter for which an anion–anion antiport mechanism was established.
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