Enzymatic resolution of (±)-epoxy-β-cyclogeraniol, a synthetic precursor for abscisic acid analogs

Ryou Okazaki; Hiromasa Kiyota; Takayuki Oritani

doi:10.1271/bbb.64.1444

Enzymatic resolution of (±)-epoxy-β-cyclogeraniol, a synthetic precursor for abscisic acid analogs

Ryou Okazaki, Hiromasa Kiyota, Takayuki Oritani

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

10 Citations (Scopus)

Abstract

Lipase-catalyzed optical resolution of (±)-epoxy-β-cyclogeraniol (1), a key synthetic intermediate for epoxy-β-ionylideneacetic acid, was achieved in high enantiomeric purity. Transesterification with vinyl acetate by using lipase P (Nagase) made enriched (-)-1, while hydrolysis of the corresponding acetate by using lipase P (Amano) afforded (+)-1 with a high E value (E=1600).

Original language	English
Pages (from-to)	1444-1447
Number of pages	4
Journal	Bioscience, Biotechnology and Biochemistry
Volume	64
Issue number	7
DOIs	https://doi.org/10.1271/bbb.64.1444
Publication status	Published - 2000
Externally published	Yes

Keywords

Abscisic acid
Epoxy-β-cyclogeraniol
Epoxy-β-ionylideneacetic acid
Lipase
Transesterification

ASJC Scopus subject areas

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

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10.1271/bbb.64.1444

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title = "Enzymatic resolution of (±)-epoxy-β-cyclogeraniol, a synthetic precursor for abscisic acid analogs",

abstract = "Lipase-catalyzed optical resolution of (±)-epoxy-β-cyclogeraniol (1), a key synthetic intermediate for epoxy-β-ionylideneacetic acid, was achieved in high enantiomeric purity. Transesterification with vinyl acetate by using lipase P (Nagase) made enriched (-)-1, while hydrolysis of the corresponding acetate by using lipase P (Amano) afforded (+)-1 with a high E value (E=1600).",

keywords = "Abscisic acid, Epoxy-β-cyclogeraniol, Epoxy-β-ionylideneacetic acid, Lipase, Transesterification",

author = "Ryou Okazaki and Hiromasa Kiyota and Takayuki Oritani",

year = "2000",

doi = "10.1271/bbb.64.1444",

language = "English",

volume = "64",

pages = "1444--1447",

journal = "Bioscience, Biotechnology and Biochemistry",

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publisher = "Japan Society for Bioscience Biotechnology and Agrochemistry",

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T1 - Enzymatic resolution of (±)-epoxy-β-cyclogeraniol, a synthetic precursor for abscisic acid analogs

AU - Okazaki, Ryou

AU - Kiyota, Hiromasa

AU - Oritani, Takayuki

PY - 2000

Y1 - 2000

N2 - Lipase-catalyzed optical resolution of (±)-epoxy-β-cyclogeraniol (1), a key synthetic intermediate for epoxy-β-ionylideneacetic acid, was achieved in high enantiomeric purity. Transesterification with vinyl acetate by using lipase P (Nagase) made enriched (-)-1, while hydrolysis of the corresponding acetate by using lipase P (Amano) afforded (+)-1 with a high E value (E=1600).

AB - Lipase-catalyzed optical resolution of (±)-epoxy-β-cyclogeraniol (1), a key synthetic intermediate for epoxy-β-ionylideneacetic acid, was achieved in high enantiomeric purity. Transesterification with vinyl acetate by using lipase P (Nagase) made enriched (-)-1, while hydrolysis of the corresponding acetate by using lipase P (Amano) afforded (+)-1 with a high E value (E=1600).

KW - Abscisic acid

KW - Epoxy-β-cyclogeraniol

KW - Epoxy-β-ionylideneacetic acid

KW - Lipase

KW - Transesterification

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DO - 10.1271/bbb.64.1444

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VL - 64

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EP - 1447

JO - Bioscience, Biotechnology and Biochemistry

JF - Bioscience, Biotechnology and Biochemistry

SN - 0916-8451

IS - 7

ER -

Enzymatic resolution of (±)-epoxy-β-cyclogeraniol, a synthetic precursor for abscisic acid analogs

Abstract

Keywords

ASJC Scopus subject areas

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