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Issue 36, 2018
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Studies on sugar puckering and glycosidic stabilities of 3′-amino-5′-carboxymethyl-3′,5′-dideoxy nucleoside mimics

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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.

Graphical abstract: Studies on sugar puckering and glycosidic stabilities of 3′-amino-5′-carboxymethyl-3′,5′-dideoxy nucleoside mimics

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Publication details

The article was received on 25 Jul 2018, accepted on 28 Aug 2018 and first published on 29 Aug 2018


Article type: Paper
DOI: 10.1039/C8OB01788C
Citation: Org. Biomol. Chem., 2018,16, 6735-6740

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

    C. Pal, A. Velusamy, Y. K. Sunkari and T. K. Chakraborty, Org. Biomol. Chem., 2018, 16, 6735
    DOI: 10.1039/C8OB01788C

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