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A Survey of the Role of Noncovalent Sulfur Interactions in Drug Design.

Abstract：

:Electron deficient, bivalent sulfur atoms have two areas of positive electrostatic potential, a consequence of the low-lying σ* orbitals of the C-S bond that are available for interaction with electron donors including oxygen and nitrogen atoms and, possibly, π-systems. Intramolecular interactions are by far the most common manifestation of this effect, which offers a means of modulating the conformational preferences of a molecule. Although a well-documented phenomenon, a priori applications in drug design are relatively sparse and this interaction, which is often isosteric with an intramolecular hydrogen-bonding interaction, appears to be underappreciated by the medicinal chemistry community. In this Perspective, we discuss the theoretical basis for sulfur σ* orbital interactions and illustrate their importance in the context of drug design and organic synthesis. The role of sulfur interactions in protein structure and function is discussed and although relatively rare, intermolecular interactions between ligand C-S σ* orbitals and proteins are illustrated.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Beno BR,Yeung KS,Bartberger MD,Pennington LD,Meanwell NA

doi

10.1021/jm501853m

subject

Has Abstract

pub_date

2015-06-11 00:00:00

pages

4383-438

issue

11

eissn

0022-2623

issn

1520-4804

journal_volume

58

pub_type

杂志文章

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