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

Takayuki Oritani, Rumi Ueda, Hiromasa Kiyota

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2106-2109
Number of pages4
JournalBioscience, Biotechnology and Biochemistry
Volume65
Issue number9
DOIs
Publication statusPublished - Sep 2001
Externally publishedYes

Fingerprint

transesterification
Lipases
Lipase
hydrolysis
acetates
synthesis
Transesterification
Hydrolysis
4-hydroxy-6-oxabicyclo(3.2.1)oct-2-en-7-one
methyl shikimate
vinyl acetate

Keywords

  • (1S*, 4R*, 5R*)-4-hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one
  • Hydrolysis
  • Lipase
  • Shikimic acid
  • Transesterification

ASJC Scopus subject areas

  • Food Science
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Biotechnology
  • Chemistry (miscellaneous)
  • Applied Microbiology and Biotechnology
  • Bioengineering

Cite this

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.

In: Bioscience, Biotechnology and Biochemistry, Vol. 65, No. 9, 09.2001, p. 2106-2109.

Research output: Contribution to journalArticle

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