Chemoenzymatic synthesis of 6‐O‐alkanoyl‐N‐alkylgluconamides
Abstract Glucono‐δ‐lactone was acylated selectively at the 6‐position by fatty acid ethyl esters in the presence of Candida antarctica lipase in refluxing tert. butyl alcohol (82°C). Upon subsequent reaction with C 16 and C 18 amines in methanol the corresponding 6‐O‐alkanoyl‐N‐alkylgluconamides sel...
| Published in: | Lipid / Fett |
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| Main Authors: | , , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
Wiley
1996
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| Subjects: | |
| Online Access: | http://dx.doi.org/10.1002/lipi.19960981203 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Flipi.19960981203 https://onlinelibrary.wiley.com/doi/pdf/10.1002/lipi.19960981203 |
| Summary: | Abstract Glucono‐δ‐lactone was acylated selectively at the 6‐position by fatty acid ethyl esters in the presence of Candida antarctica lipase in refluxing tert. butyl alcohol (82°C). Upon subsequent reaction with C 16 and C 18 amines in methanol the corresponding 6‐O‐alkanoyl‐N‐alkylgluconamides selectively precipitated. These compounds were tested as cheap substitutes for ceramides, which retain water in the human skin and are used as natural conditioners in personal care preparations. However, the four 6‐O‐alkanoyl‐N‐alkylgluconamides derivatives failed to pass the test to gel squalene. Chemoenzymatische Synthese von 6‐O‐Alkanoyl‐N‐alkylgluconamiden. Glucono‐δ‐lacton wurde an 6‐Position selektiv durch Fettsäureethylester mittels Candida antarctica‐Lipase acyliert unter Reflux von tert‐Butylalkohol (82°C). Unter fortlaufender Reaktion mit C 16 ‐ und C 18 ‐Aminen in Methanol fielen die jeweiligen 6‐O‐Alkanoyl‐N‐alkylgluconamide selektiv aus. Diese Komponenten wurden als kostengünstiger Ersatz für Ceramide untersucht, welche in der menschlichen Haut Wasser zurückhalten und als natürliche Zusatzstoffe in der Kosmetik zum Einsatz kommen. Die vier 6‐O‐Alkynoyl‐N‐alkylgluconamid‐Derivate bestanden jedoch den Test zum Erstarren von Squalen nicht. |
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