Abstract

The C₃-tetrasubstituted furanoid sugar amino acid derived linear amino acid dipeptide 8 and tetrapeptide 9 on intra-molecular cyclization afforded oxazolone pseudo-peptides 1 and 2a, respectively, with formation of oxazole ring at the C-terminus. Conformational study of 2a showed seven membered intramolecular C=O×××HN (II) hydrogen bonding leading to the γ-turn conformation which is absent in the precursor tetrapeptide 9 thus indicating the role of oxazolone ring in γ-turn formation in 2a. This fact was supported by the molecular modeling studies. The oxazolone ring containing pseudo-tetrapeptide 2a was found to be better ion transporter than pseudodi-peptide1.The ion selectivity of 2a indicated Cl^-anion-selective transport via the antiport mechanism.

Keywords: sugar amino acid, oxazolone, pseudo-peptides, peptidomimetics, ion transport

Supporting Information

How to Cite

When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Burade, S. S.; Pawar, S. V.; Saha, T.; Kumbhar, N. M.; Kotmale, A. S.; Ahmad, M.; Talukdar, P.; Dhavale, D. D. Beilstein Arch. 2019, 201949. doi:10.3762/bxiv.2019.49.v1

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.