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Literature DB >> 26318995

Tris(3-hydroxypropyl)phosphine (THPP): A mild, air-stable reagent for the rapid, reductive cleavage of small-molecule disulfides.

James McNulty¹, Venkatesan Krishnamoorthy¹, Dino Amoroso², Michael Moser².

Abstract

Tris(3-hydroxypropyl)phosphine (THPP) is demonstrated to be a versatile, water-soluble and air-stable reducing agent, allowing for the rapid, irreversible reductive cleavage of disulfide bonds in both aqueous and buffered aqueous-organic media. The reagent shows exceptional stability at biological pH under which condition it permits the rapid reduction of a wide range of differentially functionalized small-molecule disulfides.

Entities: Chemical

Keywords: Aqueous chemistry; Cystine derivative; Disulfide cleavage; Thiols; Tris-(hydroxypropyl)phosphine

Mesh：

Substances：

Year: 2015 PMID： 26318995 DOI： 10.1016/j.bmcl.2015.08.027

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

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Cited

3 in total

1. Evaluation and optimization of reduction and alkylation methods to maximize peptide identification with MS-based proteomics.

Authors: Suttipong Suttapitugsakul; Haopeng Xiao; Johanna Smeekens; Ronghu Wu
Journal: Mol Biosyst Date: 2017-11-21

2. Catalyst-free reductive cyclization of bis(2-aminophenyl) disulfide with CO₂ in the presence of BH₃NH₃ to synthesize 2-unsubstituted benzothiazole derivatives.

Authors: Xiao Li; Zhenbao Liu; Hailong Hong; Limin Han; Ning Zhu
Journal: RSC Adv Date: 2022-06-20 Impact factor: 4.036

3. Comparison of two reducing agents dithiothreitol and tris(3-hydroxypropyl)phosphine for in vitro kinetic assay of vitamin K epoxide reductase.

Authors: Kazuki Takeda; Ayuko Morita; Yoshinori Ikenaka; Shouta M M Nakayama; Mayumi Ishizuka
Journal: Vet Anim Sci Date: 2020-02-15

3 in total

Tris(3-hydroxypropyl)phosphine (THPP): A mild, air-stable reagent for the rapid, reductive cleavage of small-molecule disulfides.

1. Evaluation and optimization of reduction and alkylation methods to maximize peptide identification with MS-based proteomics.

2. Catalyst-free reductive cyclization of bis(2-aminophenyl) disulfide with CO2 in the presence of BH3NH3 to synthesize 2-unsubstituted benzothiazole derivatives.

3. Comparison of two reducing agents dithiothreitol and tris(3-hydroxypropyl)phosphine for in vitro kinetic assay of vitamin K epoxide reductase.

2. Catalyst-free reductive cyclization of bis(2-aminophenyl) disulfide with CO₂ in the presence of BH₃NH₃ to synthesize 2-unsubstituted benzothiazole derivatives.