Sugar Derived Oxazolone Pseudotetrapeptide as γ-Turn Inducer and Anion-Selective Transporter

  1. Sachin S. Burade,
  2. Sushil V. Pawar,
  3. Tanmoy Saha,
  4. Navnath M Kumbhar,
  5. Amol S. Kotmale,
  6. Manzoor Ahmad,
  7. Pinaki Talukdar and
  8. Dilip D DhavaleORCID Logo

Submitting author affiliation: Savitribai Phule Pune University (Formerly University of Pune), Pune, India

Beilstein Arch. 2019, 201949.

Published 27 Jun 2019

  • Preprint


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

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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

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