What question did this study set out to answer?

To examine the theoretical framework and practical utility of noncovalent bivalent sulfur σ* orbital interactions in drug design, organic synthesis, and protein structure.

March 3, 2015Journal of Medicinal Chemistry

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

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Authors

BBBrett R. BenoArvinas (United States)KYKap‐Sun YeungScripps Research Institute MBMichael D. BartbergerFate Therapeutics (United States)

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Implication

Review demonstrates noncovalent sulfur orbital interactions in small molecules and proteins, highlighting an underappreciated strategy to control conformation in drug design.

Key Points

To examine the theoretical framework and practical utility of noncovalent bivalent sulfur σ* orbital interactions in drug design, organic synthesis, and protein structure.
Evaluated the quantum mechanical basis of positive electrostatic potentials generated by low-lying C–S σ* orbitals in bivalent sulfur.
Surveyed structural and chemical literature for intramolecular and intermolecular sulfur–donor interactions across small molecules and protein–ligand complexes.
Bivalent sulfur atoms feature localized positive electrostatic regions capable of engaging electron donors including oxygen, nitrogen, and π-electron systems.
Intramolecular sulfur interactions reliably modulate molecular conformation and serve as effective isosteric replacements for conventional intramolecular hydrogen bonds.
Intermolecular contacts between ligand sulfur σ* orbitals and protein backbones or side chains occur naturally, offering an underused tool for rational ligand design.

Cite This Study

Beno et al. (2015) studied this question.

synapsesocial.com/papers/69d936fb8988aeabbe68475f https://doi.org/10.1021/jm501853m

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Implication

Review demonstrates noncovalent sulfur orbital interactions in small molecules and proteins, highlighting an underappreciated strategy to control conformation in drug design.

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

Discussion

Member takes

Implication

Key Points

Cite This Study

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

Discussion

Member takes

Implication

Key Points

Cite This Study

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