Convenient syntheses of [20,20,20-2H3]-arachidonic acid and [20,20,-2H2]-20-hydroxyeicosatetraenoic acid

J R Falck; Siddam Anjaiah; Venugopal Kaju Tuniki; V. Raj Gopal; Jorge H. Capdevila

doi:10.1002/jlcr.1039

Convenient syntheses of [20,20,20-²H₃]-arachidonic acid and [20,20,-²H₂]-20-hydroxyeicosatetraenoic acid

J R Falck, Siddam Anjaiah, Venugopal Kaju Tuniki, V. Raj Gopal, Jorge H. Capdevila

Biochemistry

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

2 Scopus citations

Abstract

Deuterated arachidonic acid and 20-HETE were prepared in good overall yields and high stereoselectivities. Key transformations include a trans-specific vinyl dibromide reduction and Suzuki cross-couplings to a lithium borate or a 9-BBN borane. These standards are three and two mass units higher, respectively, than their naturally occurring counterparts and are useful in mass spectrometry analysis.

Original language	English (US)
Pages (from-to)	245-252
Number of pages	8
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	49
Issue number	3
DOIs	https://doi.org/10.1002/jlcr.1039
State	Published - Mar 15 2006

Keywords

H-labeled standards
Stereoselective
Suzuki cross-coupling
Z-vinyl bromide

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Radiology Nuclear Medicine and imaging
Drug Discovery
Spectroscopy
Organic Chemistry

Access to Document

10.1002/jlcr.1039

Cite this

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title = "Convenient syntheses of [20,20,20-2H3]-arachidonic acid and [20,20,-2H2]-20-hydroxyeicosatetraenoic acid",

abstract = "Deuterated arachidonic acid and 20-HETE were prepared in good overall yields and high stereoselectivities. Key transformations include a trans-specific vinyl dibromide reduction and Suzuki cross-couplings to a lithium borate or a 9-BBN borane. These standards are three and two mass units higher, respectively, than their naturally occurring counterparts and are useful in mass spectrometry analysis.",

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AU - Anjaiah, Siddam

AU - Tuniki, Venugopal Kaju

AU - Gopal, V. Raj

AU - Capdevila, Jorge H.

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AB - Deuterated arachidonic acid and 20-HETE were prepared in good overall yields and high stereoselectivities. Key transformations include a trans-specific vinyl dibromide reduction and Suzuki cross-couplings to a lithium borate or a 9-BBN borane. These standards are three and two mass units higher, respectively, than their naturally occurring counterparts and are useful in mass spectrometry analysis.

KW - H-labeled standards

KW - Stereoselective

KW - Suzuki cross-coupling

KW - Z-vinyl bromide

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