Enzymatic syntheses of N‐lauroyl‐β‐alanine homologs in organic media

• Published in: Journal of the American Oil Chemists' Society
• Main Authors: Izumi, Taeko, Yagimuma, Yoshihiro, Haga, Masanori
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 1997
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1007/s11746-997-0231-9; https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-997-0231-9

Abstract Enyzmatic amidation of the primary amines β‐alanine ethyl ester and 3‐aminopropionitrile with methyl laurate by means of immobilized lipase ( Candida antarctica lipase, CAL) resulted in the formation in good yield of N ‐lauroyl‐β‐alanine ethyl ester and 3‐( N ‐lauroylamino)‐propionitrile, respectively. When 3‐amino‐propionitrile was used as substrate, diisopropyl ether was a suitable solvent. Changing the reaction temperature (12–80°C) did not affect the yields, and room temperature was a suitable temperature for this reaction. In the investigation of reaction conditions, the use of equimolar amounts (5 mmol) of substrate and ester, along with 0.5 g of CAL, in diisopropyl ether gave the best yield (99.3%) after 24 h of incubation at 24°C. The enzyme activity in the amidation reaction did not decrease even after six uses. With β‐alanine ethyl ester hydrochloride as substrate, diisopropyl ether was unsuited as a solvent owing to the low solubility of the substrate in this solvent. In this reaction, the best yield (82.0%) was attained by using dioxane as solvent. CAL achieved higher extents of amide synthesis with long‐chain than with short‐chain ester substrates. The enzyme accepted only nonbulky primary amines as substrates.