Synthesis of 7-thiaarachidonic acid as a mechanistic probe of prostaglandin H synthase-2

Chris M. McGinley; Cyril Jacquot; Wilfred A. van der Donk

doi:10.1016/j.bmcl.2007.04.073

Synthesis of 7-thiaarachidonic acid as a mechanistic probe of prostaglandin H synthase-2

Chris M. McGinley, Cyril Jacquot, Wilfred A. van der Donk

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

Abstract

The mechanism by which prostaglandin synthase converts arachidonic acid to prostaglandin G₂, creating five new chiral centers in the process, is still incompletely understood. The first radical intermediate has been characterized by EPR spectroscopy but subsequent proposed intermediates have not succumbed to detection. We report the synthesis of 7-thiaarachidonic acid designed to stabilize one of the proposed radical intermediates, which may allow its detection.

Original language	English (US)
Pages (from-to)	4049-4052
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	17
Issue number	14
DOIs	https://doi.org/10.1016/j.bmcl.2007.04.073
State	Published - Jul 15 2007

Keywords

Alkenyl sulfide
Arachidonic acid
Lipoxygenase
Prostaglandin synthase

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

Online availability

10.1016/j.bmcl.2007.04.073

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abstract = "The mechanism by which prostaglandin synthase converts arachidonic acid to prostaglandin G2, creating five new chiral centers in the process, is still incompletely understood. The first radical intermediate has been characterized by EPR spectroscopy but subsequent proposed intermediates have not succumbed to detection. We report the synthesis of 7-thiaarachidonic acid designed to stabilize one of the proposed radical intermediates, which may allow its detection.",

keywords = "Alkenyl sulfide, Arachidonic acid, Lipoxygenase, Prostaglandin synthase",

author = "McGinley, {Chris M.} and Cyril Jacquot and {van der Donk}, {Wilfred A.}",

note = "Funding Information: This work was supported by a pre-doctoral fellowship to C.M.M. from the American Heart Association (#0310006Z) and by the National Institutes of Health (GM44911). ",

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AU - Jacquot, Cyril

AU - van der Donk, Wilfred A.

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N2 - The mechanism by which prostaglandin synthase converts arachidonic acid to prostaglandin G2, creating five new chiral centers in the process, is still incompletely understood. The first radical intermediate has been characterized by EPR spectroscopy but subsequent proposed intermediates have not succumbed to detection. We report the synthesis of 7-thiaarachidonic acid designed to stabilize one of the proposed radical intermediates, which may allow its detection.

AB - The mechanism by which prostaglandin synthase converts arachidonic acid to prostaglandin G2, creating five new chiral centers in the process, is still incompletely understood. The first radical intermediate has been characterized by EPR spectroscopy but subsequent proposed intermediates have not succumbed to detection. We report the synthesis of 7-thiaarachidonic acid designed to stabilize one of the proposed radical intermediates, which may allow its detection.

KW - Alkenyl sulfide

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KW - Lipoxygenase

KW - Prostaglandin synthase

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Synthesis of 7-thiaarachidonic acid as a mechanistic probe of prostaglandin H synthase-2

Abstract

Keywords

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