Synthesis of gerfelin and related analogous compounds

Md Sadequl Islam; Mitsuhiro Kitagawa; Masaya Imoto; Takeshi Kitahara; Hidenori Watanabe

doi:10.1271/bbb.60287

Synthesis of gerfelin and related analogous compounds

Md Sadequl Islam, Mitsuhiro Kitagawa, Masaya Imoto, Takeshi Kitahara, Hidenori Watanabe

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

14 Citations (Scopus)

Abstract

Gerfelin, an inhibitor of human geranylgeranyl diphosphate (GGPP) synthase that has been isolated from a culture broth of Beauveria felina QN22047, was synthesized in 4 and 3 steps starting from 2,4-dihydroxy-6-methylbenzoic acid and 3,4,5-trihydroxytoluene, respectively. An effective ligand, 2-(di-tert-butyl-phosphino) biphenyl, was used in the palladium-catalyzed diaryl ether-forming reaction. Five analogous compounds of gerfelin were also synthesized for a study of the structure-activity relationship.

Original language	English
Pages (from-to)	2523-2528
Number of pages	6
Journal	Bioscience, Biotechnology and Biochemistry
Volume	70
Issue number	10
DOIs	https://doi.org/10.1271/bbb.60287
Publication status	Published - 2006
Externally published	Yes

Keywords

Enzyme inhibitor
Geranylgeranyl diphosphate synthase
Gerfelin

ASJC Scopus subject areas

Biotechnology
Analytical Chemistry
Biochemistry
Applied Microbiology and Biotechnology
Molecular Biology
Organic Chemistry

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10.1271/bbb.60287

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T1 - Synthesis of gerfelin and related analogous compounds

AU - Islam, Md Sadequl

AU - Kitagawa, Mitsuhiro

AU - Imoto, Masaya

AU - Kitahara, Takeshi

AU - Watanabe, Hidenori

PY - 2006

Y1 - 2006

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AB - Gerfelin, an inhibitor of human geranylgeranyl diphosphate (GGPP) synthase that has been isolated from a culture broth of Beauveria felina QN22047, was synthesized in 4 and 3 steps starting from 2,4-dihydroxy-6-methylbenzoic acid and 3,4,5-trihydroxytoluene, respectively. An effective ligand, 2-(di-tert-butyl-phosphino) biphenyl, was used in the palladium-catalyzed diaryl ether-forming reaction. Five analogous compounds of gerfelin were also synthesized for a study of the structure-activity relationship.

KW - Enzyme inhibitor

KW - Geranylgeranyl diphosphate synthase

KW - Gerfelin

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EP - 2528

JO - Bioscience, Biotechnology and Biochemistry

JF - Bioscience, Biotechnology and Biochemistry

IS - 10

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Synthesis of gerfelin and related analogous compounds

Abstract

Keywords

ASJC Scopus subject areas

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