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Studies on sugar puckering and glycosidic stabilities of 3 `-amino-5-carboxymethyl-3 `,5 `-dideoxy nucleoside mimics

Pal, Chandan and Velusamy, Arventh and Sunkari, Yashoda Krishna and Chakraborty, Tushar Kanti (2018) Studies on sugar puckering and glycosidic stabilities of 3 `-amino-5-carboxymethyl-3 `,5 `-dideoxy nucleoside mimics. In: ORGANIC & BIOMOLECULAR CHEMISTRY, 16 (36). pp. 6735-6740.

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Official URL: http://dx.doi.org/10.1039/c8ob01788c

Abstract

The synthesis of nucleoside amino acid monomers and dimers has been carried out to evaluate and characterize the impact of the neutral amide backbone on key attributes like puckering of the sugar rings and glycosidic bond strengths of these analogs. The conformational analysis suggests that amide-linked nucleotides have a high predilection towards N-type conformers. The glycosidic bond strength was found to be slightly weaker compared to ribonucleosides under acidic conditions at high temperatures. The results will be helpful to explore in future the development of fully amide-linked oligonucleotides for therapeutic purposes.

Item Type: Journal Article
Additional Information: Copy right for this article belong to ROYAL SOC CHEMISTRY
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 16 Oct 2018 14:23
Last Modified: 16 Oct 2018 14:23
URI: http://eprints.iisc.ac.in/id/eprint/60892

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