Synthesis of (−)-Methyl Shikimate via Enzymatic Resolution of (1S*, 4R*, 5R*)-4-Hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one

ORITANI, Takayuki; UEDA, Rumi; Kiyota, Hiromasa

Synthesis of (−)-Methyl Shikimate via Enzymatic Resolution of (1S, 4R, 5R*)-4-Hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one

2001

ORITANI, Takayuki | UEDA, Rumi | Kiyota, Hiromasa

The synthesis of methyl (−)-shikimate [(−)-2] was achieved via lipase-catalyzed optical resolution of (1S*,4R*,5R*)-4-hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one (3). Transesterification of (±)-3 and vinyl acetate with lipase MY and subsequent hydrolysis gave optically pure (−)-3. This compound was converted to (−)-2 in two steps.

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Mots clés AGROVOC

biotechnology carboxylic ester hydrolases hydrolysis lipase transesterification

Informations bibliographiques

Publié dans

Bioscience, biotechnology, and biochemistry

Volume 65 Numéro 9 Pagination 2106 - 2109 ISSN 1347-6947

Editeur

Japan Society for Bioscience, Biotechnology, and Agrochemistry

D'autres materias

Vinyl acetate; Shikimic acid; 5r*)-4-hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one; 4r*; (1s*

Langue

anglais

Note

Nal-light

Type

Journal Article; Text

Sur AGRIS depuis: 2024-02-28

Format: MODS

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Cette notice bibliographique a été fournie par National Agricultural Library

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Liens

DOI DOI http://dx.doi.org/10.1271/bbb.65.2106

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Synthesis of (−)-Methyl Shikimate via Enzymatic Resolution of (1S*, 4R*, 5R*)-4-Hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one

2001

Mots clés AGROVOC

Informations bibliographiques

Synthesis of (−)-Methyl Shikimate via Enzymatic Resolution of (1S, 4R, 5R*)-4-Hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one