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Synthesis, odour characteristics, and antibacterial activity of optically active cognac lactones
Author(s) -
Kaku Satsuki,
Hashimoto Masatoshi,
Ohtsu Naofumi,
Hoshi Masayuki,
Ogawa Narihito,
Miyakoshi Tetsuo,
Masuda Hiroyuki,
Yoshiwara Masahiro,
Fujii Koya,
Shimotori Yasutaka
Publication year - 2021
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.3670
Subject(s) - diastereomer , chemistry , enantiomer , antibacterial activity , optically active , stereochemistry , proline , antibacterial agent , organic chemistry , bacteria , amino acid , biochemistry , antibiotics , genetics , biology
In this study, all stereoisomers of cognac lactone ( 1 ) were synthesized with over 99% enantiomeric excess via diastereomeric resolution using N ‐benzyloxycarbonyl‐ l ‐proline ( N ‐Cbz‐ l ‐proline) as a resolving agent. N ‐Cbz‐ l ‐proline could be applied for the diastereomeric resolution of both syn ‐ and anti ‐forms and yielded all diastereomers in over 99% diastereomeric excess. The odour properties of racemic and optically active 1 were evaluated for their orthonasal aromas. All the stereoisomers had different odour characteristics and thresholds. In general, the (3 S )‐ and (3 R )‐forms had fruity and herbal notes, respectively, and (3 R ,4 S )‐ 1 had the lowest odour threshold at 0.01 ppm. All stereoisomers, except (3 R ,4 S )‐ 1 , showed antibacterial activity against Staphylococcus aureus . Moreover, (3 S ,4 S )‐ 1 showed high antibacterial activity against both S aureus and Escherichia coli .