The effect of ethanol on the kinetics of lipase-mediated enantioselective esterification of 4-methyloctanoic acid and the hydrolysis of its ethyl ester

• Published in: Biotechnology and bioengineering 2001-11, Vol.76 (3), p.193-199
• Main Authors: Heinsman, Nicole W. J. T., Valente, Ana M., Smienk, Henry G. F., van der Padt, Albert, Franssen, Maurice C. R., de Groot, Aede, van 't Riet, Klaas
• Format: Article
• Language: English
• Subjects: 4-methyloctanoic acid; Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; Caprylates - metabolism; enantiomeric ratio; esterification; Esterification - drug effects; Ethanol - pharmacology; Fundamental and applied biological sciences. Psychology; hydrolysis; Hydrolysis - drug effects; kinetic parameters; Kinetics; Laboratorium voor Organische chemie; Laboratory for Organic Chemistry; Lipase - metabolism; Methods. Procedures. Technologies; Molecular Conformation; Novozym 435; Organic Chemistry; Organische Chemie; Sectie Proceskunde; Sub-department of Food and Bioprocess Engineering; Temperature; VLAG
• ISSN: 0006-3592; 1097-0290
• DOI: 10.1002/bit.10008

The Novozym 435® catalyzed esterification and hydrolysis reactions of 4‐methyloctanoic acid (ethyl ester) were investigated. In both the hydrolysis and esterification reactions, the increase of ethanol concentration led to an increase in enantiomeric ratio (E). For hydrolysis of the ethyl ester, the E‐value increased from 5.5 [0% (v/v) EtOH] up to 12 [20% (v/v) EtOH]. In case of esterification, the E‐value was already 16 [14% (v/v) EtOH] and rose to 57 [73% (v/v) EtOH]. When combining these results of esterification and hydrolysis, an enantiomeric ratio of 350 can be estimated for the sequential kinetic resolution of 4‐methyloctanoic acid. In this way, enantiopure 4‐methyloctanoic acid could be obtained after two consecutive reaction steps. © 2001 John Wiley & Sons, Inc. Biotechnol Bioeng 76: 193–199, 2001.