Glycosidic Bond Expanded Cyclic Oligosaccharides: Synthesis and Host-Guest Binding Property of a Cyclic Pentasaccharide

Samanta, Gopal Ch and Maiti, Krishnagopal and Jayaraman, Narayanaswamy (2018) Glycosidic Bond Expanded Cyclic Oligosaccharides: Synthesis and Host-Guest Binding Property of a Cyclic Pentasaccharide. In: ACS OMEGA, 3 (7). pp. 7466-7473.

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Abstract

A new cyclic pentasaccharide comprising an oxymethylene glycosidic bond connecting the individual alpha-D-glycopyranoside monomers is synthesized through cyclo-glycosylation of a linear pentasaccharide precursor, which, in turn, is synthesized through the block glycosylation method. Molecular modeling shows that the 30-membered macrocyclic pentasaccharide is a distorted ellipsoid structure, with the lower and upper rims occupied by secondary and primary hydroxyl groups, respectively. Following the synthesis, the microenvironment of the cyclic pentasaccharide is assessed through thermodynamic evaluation upon complexation with 1-aminoadamantane in an aqueous solution, which shows the formation of similar to 1:2 host-to-guest complex and a binding affinity of 10 500 (+/- 425) M-1. Synthesis and assessment of the host-guest binding property of the new glycosidic bond expanded cyclic pentasaccharide are presented.

Item Type:	Journal Article
Publication:	ACS OMEGA
Publisher:	AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Additional Information:	Copyright of this article belong to AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	10 Aug 2018 16:08
Last Modified:	10 Aug 2018 16:08
URI:	http://eprints.iisc.ac.in/id/eprint/60401

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