Abstract
Racemic 2-, 3- and 4-methyloctanoic acids were synthesized. The 2-mercaptoethanol S-esters of these branched acids, and of octanoic acid, were exposed to lipases of the fungiCandida rugosa andAspergillus niger. Reactions were followed spectrophotometrically using Ellman's Reagent. Branching at the 3-position retards lipolysis more severely than at either the 2- or 4-positions. Features of the assay method are discussed with reference to titrimetry.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
Abbreviations
- DTNB:
-
5,5′-dithio-bis-(2-nitrobenzoic) acid
- GLC:
-
gas-liquid chromatography
- HMPT:
-
hexamethyl phosphoric triamide
- IR:
-
infrared
- LDA:
-
lithium diisopropylamide
- MS:
-
mass spectra
- NMR:
-
nuclear magnetic resonance
- Vi :
-
initial velocity
- Vmax :
-
maximum velocity
References
Sonnet, P.E., Piotrowski, E.G., and Boswell, R.T. (1988)J. Chromatogr. 436, 205–217.
Kirchner, G., Scollar, M.P., and Klibanov, A.M. (1985)J. Am. Chem. Soc. 107, 7072–7076.
Brockerhoff, H., and Jensen, R.G. (1974)Lipolytic Enzymes, pp. 64–65, Academic Press, New York.
Japan Patent 894,294 (1982).
Cambou, B., and Klibanov, A.M. (1984)Biotech. Bioeng. XXVI, 1449–1454.
Cambou, B., and Klibanov, A.M. (1984)Biochem. and Biotech. 9, 255–260.
U.S. Patent 4,601,987 (1986).
Dahod, S.K., and Mangeno, P.S. (1987)Biotech Bioeng. XXX, 995–999.
Inada, Y., Takahashi, K., Yashimoto, T., Ajima, A., Matsushima, A., and Saito, Y. (1986)Tibtech 190–194.
Cox, J.W., and Horrocks, L.A. (1981)J. Lipid Research 22, 495–505.
Renard, G., Grimaud, J., El Zant, A., Pina, M., and Graille, J. (1987)Lipids 22, 539–541.
Pfeffer, P.E., and Silbert, L.S. (1970)J. Org. Chem. 35, 262–264.
Meyers, A.I., Poindexter, G.S., and Brich, Z. (1978)J. Org. Chem. 43, 892–898.
DeKimpe, N., and Schamp, N. (1975)J. Org. Chem. 40, 3749–3756.
Heide, R., de Valois, P.J., Wobben, H.J., and Timmer, R. (1975)J. Agric. Food Chem. 23, 57–60.
Stork, G., and Dowd, S. (1963)J. Am. Chem. Soc. 85, 2178–2180.
Wong, E., Nixon, L.N., and Johnson, C.B. (1975)J. Agric. Food Chem. 23, 495–498.
Annisuzzaman, A.K.M., and Owen, L.N. (1967)J. Chem. Soc. (C) 1021–1026.
Sonnet, P.E., and Antonian, E. (in press)J. Agric. Food Chem.
Furukawa, I., Kuruoka, S., Arisue, K., Kohda, K., and Hayashi, C. (1982)Clin. Chem. 28, 110–113.
Rick, W., and Hockeborn, M. (1982)J. Clin. Chem. Clin. Biochem. 20, 537–552.
Author information
Authors and Affiliations
About this article
Cite this article
Sonnet, P.E., Baillargeon, M.W. Synthesis and lipase catalyzed hydrolysis of thiolesters of 2-, 3- and 4-methyl octanoic acids. Lipids 24, 434–437 (1989). https://doi.org/10.1007/BF02535152
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02535152