Details

Autor(en) / Beteiligte

• Cavaille-Lefebvre, D
• Combes, D
• Rehbock, B
• Berger, R.G

Titel

chromatographic and mass-spectrometric approach for the analysis of lipase-produced thioester derivatives

Ist Teil von

• Applied microbiology and biotechnology, 1998-02, Vol.49 (2), p.136-140

Ort / Verlag

Berlin: Springer

Erscheinungsjahr

1998

Quelle

2022 ECC(Springer)

Beschreibungen/Notizen

• 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.