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

School of Pharmaceutical Sciences

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

3 Citations (Scopus)

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.

Original language	English
Pages (from-to)	396-400
Number of pages	5
Journal	Bioscience, Biotechnology and Biochemistry
Volume	62
Issue number	2
DOIs	https://doi.org/10.1271/bbb.62.396
Publication status	Published - 1998

Keywords

dihydrodihydroxyphthalic acid
hydrolysis
meso substrate
photooxygenation
pig pancreatic lipase

ASJC Scopus subject areas

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

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10.1271/bbb.62.396

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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.",

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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",

volume = "62",

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

Abstract

Keywords

ASJC Scopus subject areas

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