Reductive ligation mediated one-step disulfide formation of S -nitrosothiols

Jiming Zhang; Sheng Li; Dehui Zhang; Hua Wang; A. Richard Whorton; Ming Xian

doi:10.1021/ol101863s

Reductive ligation mediated one-step disulfide formation of S -nitrosothiols

Jiming Zhang, Sheng Li, Dehui Zhang, Hua Wang, A. Richard Whorton, Ming Xian

Research output: Contribution to journal › Article › peer-review

55 Scopus citations

Abstract

A one-step reductive ligation mediated disulfide formation of S-nitrosothiols was developed. This reaction involves the reaction of the S-nitroso group with phosphine-thioesters to form sulfenamide and thiolate intermediates, which then undergo a fast intermolecular disulfide formation to form stable conjugates. This reaction can be used to design new biosensors of S-nitrosated proteins.

Original language	English (US)
Pages (from-to)	4208-4211
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	18
DOIs	https://doi.org/10.1021/ol101863s
State	Published - Sep 17 2010
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol101863s

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title = "Reductive ligation mediated one-step disulfide formation of S -nitrosothiols",

abstract = "A one-step reductive ligation mediated disulfide formation of S-nitrosothiols was developed. This reaction involves the reaction of the S-nitroso group with phosphine-thioesters to form sulfenamide and thiolate intermediates, which then undergo a fast intermolecular disulfide formation to form stable conjugates. This reaction can be used to design new biosensors of S-nitrosated proteins.",

author = "Jiming Zhang and Sheng Li and Dehui Zhang and Hua Wang and Whorton, {A. Richard} and Ming Xian",

year = "2010",

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doi = "10.1021/ol101863s",

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T1 - Reductive ligation mediated one-step disulfide formation of S -nitrosothiols

AU - Zhang, Jiming

AU - Li, Sheng

AU - Zhang, Dehui

AU - Wang, Hua

AU - Whorton, A. Richard

AU - Xian, Ming

PY - 2010/9/17

Y1 - 2010/9/17

N2 - A one-step reductive ligation mediated disulfide formation of S-nitrosothiols was developed. This reaction involves the reaction of the S-nitroso group with phosphine-thioesters to form sulfenamide and thiolate intermediates, which then undergo a fast intermolecular disulfide formation to form stable conjugates. This reaction can be used to design new biosensors of S-nitrosated proteins.

AB - A one-step reductive ligation mediated disulfide formation of S-nitrosothiols was developed. This reaction involves the reaction of the S-nitroso group with phosphine-thioesters to form sulfenamide and thiolate intermediates, which then undergo a fast intermolecular disulfide formation to form stable conjugates. This reaction can be used to design new biosensors of S-nitrosated proteins.

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M3 - Article

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JO - Organic Letters

JF - Organic Letters

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ER -

Reductive ligation mediated one-step disulfide formation of S -nitrosothiols

Abstract

ASJC Scopus subject areas

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