Details
| Original language | English |
|---|---|
| Pages (from-to) | 136-140 |
| Number of pages | 5 |
| Journal | Applied Microbiology and Biotechnology |
| Volume | 49 |
| Issue number | 2 |
| Publication status | Published - Feb 1998 |
Abstract
The synthesis of thioethyl 2-methylpropanoate, butanoate, 3-methylbutanoate, hexanoate, and of thiobutyl propanoate, butanoate, and pentanoate was achieved via esterification of ethanethiol or butanethiol with short-chain acids using an immobilised lipase from Rhizomucor miehei. High acid conversions were obtained (47% for thiobutyl pentanoate). The analysis of educts and products was carried out by reverse-phase liquid chromatography (HPLC), gas chromatography (GC), GC/mass spectrometry, and GC/olfactometry. All of the thioesters imparted a similar, onion-like smell, which remained unchanged on dilution. The thresholds of thioesters derived from the same thiol were loosely correlated with the size of the acid moiety: the larger the molecular mass the higher the threshold. Surprisingly, higher odour thresholds were obtained for the branched-chain thioesters than for their linear analogues.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biotechnology
- Immunology and Microbiology(all)
- Applied Microbiology and Biotechnology
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In: Applied Microbiology and Biotechnology, Vol. 49, No. 2, 02.1998, p. 136-140.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - A chromatographic and mass-spectrometric approach for the analysis of lipase-produced thioester derivatives
AU - Cavaillé-Lefebvre, D.
AU - Combes, D.
AU - Rehbock, B.
AU - Berger, R. G.
PY - 1998/2
Y1 - 1998/2
N2 - The synthesis of thioethyl 2-methylpropanoate, butanoate, 3-methylbutanoate, hexanoate, and of thiobutyl propanoate, butanoate, and pentanoate was achieved via esterification of ethanethiol or butanethiol with short-chain acids using an immobilised lipase from Rhizomucor miehei. High acid conversions were obtained (47% for thiobutyl pentanoate). The analysis of educts and products was carried out by reverse-phase liquid chromatography (HPLC), gas chromatography (GC), GC/mass spectrometry, and GC/olfactometry. All of the thioesters imparted a similar, onion-like smell, which remained unchanged on dilution. The thresholds of thioesters derived from the same thiol were loosely correlated with the size of the acid moiety: the larger the molecular mass the higher the threshold. Surprisingly, higher odour thresholds were obtained for the branched-chain thioesters than for their linear analogues.
AB - The synthesis of thioethyl 2-methylpropanoate, butanoate, 3-methylbutanoate, hexanoate, and of thiobutyl propanoate, butanoate, and pentanoate was achieved via esterification of ethanethiol or butanethiol with short-chain acids using an immobilised lipase from Rhizomucor miehei. High acid conversions were obtained (47% for thiobutyl pentanoate). The analysis of educts and products was carried out by reverse-phase liquid chromatography (HPLC), gas chromatography (GC), GC/mass spectrometry, and GC/olfactometry. All of the thioesters imparted a similar, onion-like smell, which remained unchanged on dilution. The thresholds of thioesters derived from the same thiol were loosely correlated with the size of the acid moiety: the larger the molecular mass the higher the threshold. Surprisingly, higher odour thresholds were obtained for the branched-chain thioesters than for their linear analogues.
UR - http://www.scopus.com/inward/record.url?scp=0031886147&partnerID=8YFLogxK
U2 - 10.1007/s002530051149
DO - 10.1007/s002530051149
M3 - Article
AN - SCOPUS:0031886147
VL - 49
SP - 136
EP - 140
JO - Applied Microbiology and Biotechnology
JF - Applied Microbiology and Biotechnology
SN - 0175-7598
IS - 2
ER -