A survey of the role of noncovalent sulfur interactions in drug design

BR Beno, KS Yeung, MD Bartberger… - Journal of medicinal …, 2015 - ACS Publications
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 …

Insights into thiol–aromatic interactions: a stereoelectronic basis for S–H/π interactions

CR Forbes, SK Sinha, HK Ganguly, S Bai… - Journal of the …, 2017 - ACS Publications
Thiols can engage favorably with aromatic rings in S–H/π interactions, within abiological
systems and within proteins. However, the underlying bases for S–H/π interactions are not …

Hypervalent nonbonded interactions of a divalent sulfur atom. Implications in protein architecture and the functions

M Iwaoka, N Isozumi - Molecules, 2012 - mdpi.com
In organic molecules a divalent sulfur atom sometimes adopts weak coordination to a
proximate heteroatom (X). Such hypervalent nonbonded S··· X interactions can control the …

Statistical and theoretical investigations on the directionality of nonbonded S⊙⊙⊙ O interactions. Implications for molecular design and protein engineering

M Iwaoka, S Takemoto, S Tomoda - Journal of the American …, 2002 - ACS Publications
Weak nonbonded interactions between a divalent sulfur (S) atom and a main-chain carbonyl
oxygen (O) atom have recently been characterized in proteins. However, they have shown …

How do we address neglected sulfur pharmacophores in drug discovery?

MJ Tilby, MC Willis - Expert Opinion on Drug Discovery, 2021 - Taylor & Francis
Sulfur is an ubiquitous heteroatom in medicinal chemistry [1]. Its prevalence is often credited
to its ability to exist in many oxidation states, whilst also being capable of bonding to a …

The importance of sulfur-containing motifs in drug design and discovery

M Mustafa, JY Winum - Expert opinion on drug discovery, 2022 - Taylor & Francis
Introduction Sulfur-containing functional groups are privileged motifs that occur in various
pharmacologically effective substances and several natural products. Various functionalities …

Simultaneous σ‐hole and hydrogen bonding by sulfur‐and selenium‐containing heterocycles

JS Murray, P Lane, P Politzer - International Journal of …, 2008 - Wiley Online Library
Abstract When a Group V, VI, or VII atom forms a covalent bond, its bonding orbital has a
deficiency of electronic charge in its outer (noninvolved) lobe. This is called a σ‐hole. If the …

Nature and strength of sulfur-centred hydrogen bonds: laser spectroscopic investigations in the gas phase and quantum-chemical calculations

HS Biswal, S Bhattacharyya… - … Reviews in Physical …, 2015 - Taylor & Francis
The importance of Sulfur centred hydrogen bonds (SCHBs) cannot be underestimated given
the current day knowledge of its non-covalent interactions prevalent in many biopolymers as …

Multifaceted roles of disulfide bonds. Peptides as therapeutics

M Gongora-Benitez, J Tulla-Puche… - Chemical Reviews, 2014 - ACS Publications
In the last century, small-molecule natural products were the main inspiration for most drug
discovery programs based either on high-throughput screening (HTS) or rational design …

Estimates of the ab Initio Limit for Sulfur−π Interactions:  The H2S−Benzene Dimer

TP Tauer, ME Derrick, CD Sherrill - The Journal of Physical …, 2005 - ACS Publications
The interaction between aromatic rings and sulfur atoms in the side chains of amino acids is
a factor in the formation and stabilization of α-helices in proteins. We studied the H2S …