Issue 40, 2013
From the journal:

Organic & Biomolecular Chemistry

Sugar furanoid trans-vicinal diacid as a γ-turn inducer: synthesis and conformational study†

Madhuri Vangala,a   Snehal A. Dhokale,b   Rupesh L. Gawade,c   Rajamohanan R. Pattuparambil,b   Vedavati G. Puranikc  and  Dilip D. Dhavale*a  

* Corresponding authors

a Department of Chemistry, Garware Research Centre, University of Pune, Pune, India
E-mail: ddd@chem.unipune.ac.in

b Central NMR Facility, National Chemical Laboratory, Dr Homi Bhabha Road, Pune 411 008, India

c Centre for Materials Characterization, National Chemical Laboratory, Dr Homi Bhabha Road, Pune 411 008, India

Abstract

A simple method for the synthesis of a sugar furanoid trans vicinal diacid and its incorporation into the N-terminal tetrapeptide sequence (H-Phe-Trp-Lys-Thr-OH) to get glycopeptide 8 has been described. 2D NMR and MD simulation studies of 8 clearly show that the sugar diacid adopts a γ-turn conformation towards the N-terminus.

Graphical abstract: Sugar furanoid trans-vicinal diacid as a γ-turn inducer: synthesis and conformational study

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Article information

DOI
https://doi.org/10.1039/C3OB41462K
Article type
Communication
Submitted
16 Jul 2013
Accepted
05 Aug 2013
First published
07 Aug 2013

Org. Biomol. Chem., 2013,11, 6874-6878

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Sugar furanoid trans-vicinal diacid as a γ-turn inducer: synthesis and conformational study

M. Vangala, S. A. Dhokale, R. L. Gawade, R. R. Pattuparambil, V. G. Puranik and D. D. Dhavale, Org. Biomol. Chem., 2013, 11, 6874 DOI: 10.1039/C3OB41462K

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