Issue 36, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
25 Jul 2018
Accepted
28 Aug 2018
First published
29 Aug 2018

Org. Biomol. Chem., 2018,16, 6735-6740

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements