Asymmetric synthesis of  δ ‐lactones with lipase catalyst | Zendy

Shimotori Yasutaka | Zendy; Sekine Kazuki | Zendy; Miyakoshi Tetsuo | Zendy

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Asymmetric synthesis of δ ‐lactones with lipase catalyst

Author(s) -

Shimotori Yasutaka,

Sekine Kazuki,

Miyakoshi Tetsuo

Publication year - 2007

Publication title -

flavour and fragrance journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.393

H-Index - 70

eISSN - 1099-1026

pISSN - 0882-5734

DOI - 10.1002/ffj.1836

Subject(s) - chemistry , acetylation , enantiomer , lipase , hydrolysis , catalysis , triacylglycerol lipase , enantioselective synthesis , pancreatic lipase , enantiomeric excess , organic chemistry , stereochemistry , enzyme , biochemistry , gene

Both enantiomers of δ ‐lactones ( δ ‐decalactone, δ ‐undecalactone and δ ‐dodecalactone) were synthesized in three steps via Novozym 435‐catalysed acetylation of rac ‐ N ‐methyl‐5‐hydroxyalkylamides with about 80% e.e. The enantiomeric excess of δ ‐lactones was increased to 89–99% e.e. by substitution of porcine pancreatic lipase (PPL)‐catalysed hydrolysis of rac ‐ N ‐methyl‐5‐acetoxyalkylamides for Novozym 435‐catalysed acetylation of rac ‐ N ‐methyl‐5‐hydroxyalkylamides. Copyright © 2007 John Wiley & Sons, Ltd.

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