Syntheses of Highly Oxygen-functionalized Derivatives of Dihydrodihydroxyphthalic Acid in Enantiomerically Enriched Forms

Hajime Ikeda; Hiroyuki Hosomi; Shigeru Ohba; Hiromichi Ohta; Takeshi Sugai

doi:10.1271/bbb.62.396

Syntheses of Highly Oxygen-functionalized Derivatives of Dihydrodihydroxyphthalic Acid in Enantiomerically Enriched Forms

Hajime Ikeda
, Hiroyuki Hosomi
, Shigeru Ohba
, Hiromichi Ohta
, Takeshi Sugai

薬科学科

研究成果: Article › 査読

3 被引用数 (Scopus)

抄録

Starting from dihydrodihydroxyphthalic acid (DDP), (1R, 2S, 5R, 6S))-(-)-3,4-bis(benzyloxymethyl)-5-hydroxy-8,8-dimethyl-6,8-dioxabicyelo[4.3.0]non-3-en-2-yl chloroacetate (>95%e.e.), a highly oxygen-functionalized derivative, was prepared by a combination of chemical and enzymatic reactions. The key step for asymmetrization was hydrolysis of the corresponding meso bis-chloroacetate with pig pancreatic lipase.

本文言語	English
ページ（範囲）	396-400
ページ数	5
ジャーナル	Bioscience, Biotechnology and Biochemistry
巻	62
号	2
DOI	https://doi.org/10.1271/bbb.62.396
出版ステータス	Published - 1998

ASJC Scopus subject areas

医学一般

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title = "Syntheses of Highly Oxygen-functionalized Derivatives of Dihydrodihydroxyphthalic Acid in Enantiomerically Enriched Forms",

abstract = "Starting from dihydrodihydroxyphthalic acid (DDP), (1R, 2S, 5R, 6S))-(-)-3,4-bis(benzyloxymethyl)-5-hydroxy-8,8-dimethyl-6,8-dioxabicyelo[4.3.0]non-3-en-2-yl chloroacetate (>95\%e.e.), a highly oxygen-functionalized derivative, was prepared by a combination of chemical and enzymatic reactions. The key step for asymmetrization was hydrolysis of the corresponding meso bis-chloroacetate with pig pancreatic lipase.",

keywords = "dihydrodihydroxyphthalic acid, hydrolysis, meso substrate, photooxygenation, pig pancreatic lipase",

author = "Hajime Ikeda and Hiroyuki Hosomi and Shigeru Ohba and Hiromichi Ohta and Takeshi Sugai",

year = "1998",

doi = "10.1271/bbb.62.396",

language = "English",

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pages = "396--400",

journal = "Bioscience, Biotechnology and Biochemistry",

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T1 - Syntheses of Highly Oxygen-functionalized Derivatives of Dihydrodihydroxyphthalic Acid in Enantiomerically Enriched Forms

AU - Ikeda, Hajime

AU - Hosomi, Hiroyuki

AU - Ohba, Shigeru

AU - Ohta, Hiromichi

AU - Sugai, Takeshi

PY - 1998

Y1 - 1998

N2 - Starting from dihydrodihydroxyphthalic acid (DDP), (1R, 2S, 5R, 6S))-(-)-3,4-bis(benzyloxymethyl)-5-hydroxy-8,8-dimethyl-6,8-dioxabicyelo[4.3.0]non-3-en-2-yl chloroacetate (>95%e.e.), a highly oxygen-functionalized derivative, was prepared by a combination of chemical and enzymatic reactions. The key step for asymmetrization was hydrolysis of the corresponding meso bis-chloroacetate with pig pancreatic lipase.

AB - Starting from dihydrodihydroxyphthalic acid (DDP), (1R, 2S, 5R, 6S))-(-)-3,4-bis(benzyloxymethyl)-5-hydroxy-8,8-dimethyl-6,8-dioxabicyelo[4.3.0]non-3-en-2-yl chloroacetate (>95%e.e.), a highly oxygen-functionalized derivative, was prepared by a combination of chemical and enzymatic reactions. The key step for asymmetrization was hydrolysis of the corresponding meso bis-chloroacetate with pig pancreatic lipase.

KW - dihydrodihydroxyphthalic acid

KW - hydrolysis

KW - meso substrate

KW - photooxygenation

KW - pig pancreatic lipase

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M3 - Article

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SN - 0916-8451

VL - 62

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EP - 400

JO - Bioscience, Biotechnology and Biochemistry

JF - Bioscience, Biotechnology and Biochemistry

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Syntheses of Highly Oxygen-functionalized Derivatives of Dihydrodihydroxyphthalic Acid in Enantiomerically Enriched Forms

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