Issue 15, 2009
From the journal:

Chemical Communications

A conformational transition in the structure of a 2′-thiomethyl-modified DNA visualized at high resolution†

Pradeep S. Pallan,a   Thazha P. Prakash,b   Feng Li,a   Robert L. Eoff,a   Muthiah Manoharanc  and  Martin Egli*a  

* Corresponding authors

a Department of Biochemistry, Vanderbilt University School of Medicine, Nashville, USA
E-mail: martin.egli@vanderbilt.edu
Fax: +1 615 322 7122

b Department of Medicinal Chemistry, ISIS Pharmaceuticals Inc., Carlsbad, USA

c Department of Drug Discovery, Alnylam Pharmaceuticals Inc., Cambridge, USA

Abstract

Crystal structures of A-form and B-form DNA duplexes containing 2′-S-methyl-uridines reveal that the modified residues adopt a RNA-like C3′-endo pucker, illustrating that the replacement of electronegative oxygen at the 2′-carbon of RNA by sulfur does not appear to fundamentally alter the conformational preference of the sugar in the oligonucleotide context and sterics trump stereoelectronics.

Graphical abstract: A conformational transition in the structure of a 2′-thiomethyl-modified DNA visualized at high resolution

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Article information

DOI
https://doi.org/10.1039/B822781K
Article type
Communication
Submitted
18 Dec 2008
Accepted
30 Jan 2009
First published
26 Feb 2009

Chem. Commun., 2009, 2017-2019

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A conformational transition in the structure of a 2′-thiomethyl-modified DNA visualized at high resolution

P. S. Pallan, T. P. Prakash, F. Li, R. L. Eoff, M. Manoharan and M. Egli, Chem. Commun., 2009, 2017 DOI: 10.1039/B822781K

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