Lipase-catalysed resolution of γ- and δ-lactones

Journal of Biotechnology

Volumn 56, Issue 2, 1997, Pages 129-133

  Enzelberger, Markus M ^a   Bornscheuer, Uwe T ^a   Gatfield, Ian ^b   Schmid, Rolf D ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

^b Haarmann and Reimer GmbH   (Germany)

Author keywords

Lactones; Lipase; Pseudomonas species; Stereoselective hydrolysis

Indexed keywords

LACTONE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; ENANTIOMER; ENZYME ACTIVITY; FLAVOR; NONHUMAN; PRIORITY JOURNAL; PSEUDOMONAS; STEREOCHEMISTRY;

CANDIDA; CHROMOBACTERIUM; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; ISOMERISM; LACTONES; LIPASE; MOLECULAR STRUCTURE; PSEUDOMONAS; TEMPERATURE;

PSEUDOMONAS;

BACTERIA; BIOCONVERSION; CATALYSIS; CATALYST SELECTIVITY; HYDROLYSIS; PH EFFECTS; REACTION KINETICS; THERMAL EFFECTS;

LACTONES; LIPASE; PSEUDOMONAS SPECIES; STEREOSELECTIVE HYDROLYSIS;

ENZYMES;

EID: 0030616307     PISSN: 01681656     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0168-1656(97)00107-7     Document Type: Article

References (10)

1. Blanco, L., Guibé-Jampel, E., Rousseau, G., 1988. Enzymatic resolution of racemic lactones. Tetrahedron Lett. 29, 1915-1918.
2. Chen, C.S., Fujimoto, Y., Girdaukas, G., Sih, C.J., 1982. Quantitative analyses of biochemical kinetic resolutions of enantiomers. J. Am. Chem. Soc. 104, 7294-7299.
3. Gutman, A.L., Zuobi, K., Boltanski, A., 1987. Enzymatic lactonisation of γ-hydroxyesters in organic solvents. Synthesis of optically pure γ-methylbutyrolactone and γ-phenylbutyrolactone. Tetrahedron Lett. 28, 3861-3864.
4. Gutman, A.L., Zuobi, K., Bravdo, T., 1990a. Lipase-catalyzed preparation of optically active γ-butyrolactones in organic solvents. J. Org. Chem. 55, 3546-3552.
5. Gutman, A.L., Zuobi, K., Guibé-Jampel, E., 1990b. Lipase-catalysed hydrolysis of γ-substituted α-aminobutyrolactones. Tetrahedron Lett. 31, 2037-2038.
6. Kazlauskas, R.J., Weissfloch, A.N.E., Rappaport, A.T., Cuccia, L.A., 1991. A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase, lipase from Pseudomonas cepacia, and lipase from Candida rugosa. J. Org. Chem. 56, 2656-2665.
7. Shimizu, S., Kataoka, M., 1996. Structure, function, and application of microbial lactonases. Chimia 50, 409-410.
8. Uemura, T., Furukawa, M., Kodera, Y., Hiroto, M., Matsushima, A., Kuno, H., Matsushita, H., Sakurai, K., Inada, Y., 1995. Polyethylene glycol-modified lipase catalyzes asymmetric alcoholysis of δ-decalactone in n-decanol. Biotechnol. Lett. 17, 61-66.
9. Viazzo, P., Alphand, V., Furstoss, R., 1996. Microbiological transformations 34: Enantioselective hydrolysis of a keylactone involved in the synthesis of the antidepressant Milnacipran. Tetrahedron Lett. 37, 4519-4522.
10. Werkhoff, P., Brennecke, S., Bretschneider, W., Güntert, M., Hopp, R., Surburg, H., 1993. Chirospecific analysis in essential oil, fragrance and flavour research. Z. Lebensm. Unters. Forsch. 196, 307-328.