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Literature DB >> 30520644

Phosphite Esters: Reagents for Exploring S-Nitrosothiol Chemistry.

Chunrong Liu^1,2, Chung-Min Park^2,3, Difei Wang⁴, Ming Xian².

Abstract

The reactions between S-nitrosothiols and phosphite esters, including P(OPh)3, P(OBn)3, and P(OEt)3, were studied. Two different conjugated adducts, thiophosphoramidates and phosphorothioates, were formed, depending on the structures of the S-nitrosothiol substrate (e.g., primary vs tertiary). These reactions proceeded under mild conditions, and the reaction mechanisms were studied using experiments and calculations.

Entities: Chemical Gene

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Year: 2018 PMID： 30520644 PMCID： PMC6465146 DOI： 10.1021/acs.orglett.8b03393

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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References

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Phosphite Esters: Reagents for Exploring S-Nitrosothiol Chemistry.

1. S-nitrosylation: spectrum and specificity.

Review 2. The biochemistry and physiology of S-nitrosothiols.

Review 3. Nitrosylation. the prototypic redox-based signaling mechanism.

Review 4. S-nitrosylation: physiological regulation of NF-kappaB.

5. Staudinger-phosphonite reactions for the chemoselective transformation of azido-containing peptides and proteins.

Review 6. Protein S-Nitrosylation: Determinants of Specificity and Enzymatic Regulation of S-Nitrosothiol-Based Signaling.

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