Practical, enantiospecific syntheses of 14,15-EET and leukotoxin B (vernolic acid)

J R Falck; Y. Krishna Reddy; Donovan C. Haines; Komandla Malla Reddy; U. Murali Krishna; Sandra Graham; Barbara Murry; Julian A. Peterson

doi:10.1016/S0040-4039(01)00694-3

Practical, enantiospecific syntheses of 14,15-EET and leukotoxin B (vernolic acid)

J R Falck, Y. Krishna Reddy, Donovan C. Haines, Komandla Malla Reddy, U. Murali Krishna, Sandra Graham, Barbara Murry, Julian A. Peterson

Biochemistry

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

38 Scopus citations

Abstract

Cytochrome P450BM3 and its F87V mutant were exploited for a convenient, laboratory scale (1 mmol) preparation of 14(S),15(R)-epoxyeicosatrienoic acid [14(S),15(R)-EET] from arachidonic acid and (+)-leukotoxin B [(+)-12(S),13(R)-vernolic acid] from linoleic acid, respectively. Their enantiomers were accessed via a four-step chemical inversion.

Original language	English (US)
Pages (from-to)	4131-4133
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	25
DOIs	https://doi.org/10.1016/S0040-4039(01)00694-3
State	Published - Jun 18 2001

Keywords

Asymmetric synthesis
Biosynthesis
Eicosanoids
Epoxides
Inversion reactions

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)00694-3

Cite this

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title = "Practical, enantiospecific syntheses of 14,15-EET and leukotoxin B (vernolic acid)",

abstract = "Cytochrome P450BM3 and its F87V mutant were exploited for a convenient, laboratory scale (1 mmol) preparation of 14(S),15(R)-epoxyeicosatrienoic acid [14(S),15(R)-EET] from arachidonic acid and (+)-leukotoxin B [(+)-12(S),13(R)-vernolic acid] from linoleic acid, respectively. Their enantiomers were accessed via a four-step chemical inversion.",

keywords = "Asymmetric synthesis, Biosynthesis, Eicosanoids, Epoxides, Inversion reactions",

author = "Falck, {J R} and Reddy, {Y. Krishna} and Haines, {Donovan C.} and Reddy, {Komandla Malla} and Krishna, {U. Murali} and Sandra Graham and Barbara Murry and Peterson, {Julian A.}",

note = "Funding Information: Supported financially by the USPHS NIH (GM31278, DK38226, GM50858), the Robert A. Welch Foundation, and an unrestricted grant from Taisho Pharmaceutical. Copyright: Copyright 2007 Elsevier B.V., All rights reserved.",

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doi = "10.1016/S0040-4039(01)00694-3",

language = "English (US)",

volume = "42",

pages = "4131--4133",

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T1 - Practical, enantiospecific syntheses of 14,15-EET and leukotoxin B (vernolic acid)

AU - Falck, J R

AU - Reddy, Y. Krishna

AU - Haines, Donovan C.

AU - Reddy, Komandla Malla

AU - Krishna, U. Murali

AU - Graham, Sandra

AU - Murry, Barbara

AU - Peterson, Julian A.

N1 - Funding Information: Supported financially by the USPHS NIH (GM31278, DK38226, GM50858), the Robert A. Welch Foundation, and an unrestricted grant from Taisho Pharmaceutical. Copyright: Copyright 2007 Elsevier B.V., All rights reserved.

PY - 2001/6/18

Y1 - 2001/6/18

N2 - Cytochrome P450BM3 and its F87V mutant were exploited for a convenient, laboratory scale (1 mmol) preparation of 14(S),15(R)-epoxyeicosatrienoic acid [14(S),15(R)-EET] from arachidonic acid and (+)-leukotoxin B [(+)-12(S),13(R)-vernolic acid] from linoleic acid, respectively. Their enantiomers were accessed via a four-step chemical inversion.

AB - Cytochrome P450BM3 and its F87V mutant were exploited for a convenient, laboratory scale (1 mmol) preparation of 14(S),15(R)-epoxyeicosatrienoic acid [14(S),15(R)-EET] from arachidonic acid and (+)-leukotoxin B [(+)-12(S),13(R)-vernolic acid] from linoleic acid, respectively. Their enantiomers were accessed via a four-step chemical inversion.

KW - Asymmetric synthesis

KW - Biosynthesis

KW - Eicosanoids

KW - Epoxides

KW - Inversion reactions

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U2 - 10.1016/S0040-4039(01)00694-3

DO - 10.1016/S0040-4039(01)00694-3

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SN - 0040-4039

VL - 42

SP - 4131

EP - 4133

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 25

ER -

Practical, enantiospecific syntheses of 14,15-EET and leukotoxin B (vernolic acid)

Abstract

Keywords

ASJC Scopus subject areas

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