Lactones 291. Enzymatic resolution of racemic γ-lactones

Biocatalysis and Biotransformation

Volumn 25, Issue 1, 2007, Pages 79-83

  Fajkowska, Małgorzata ^a   Obara, Robert ^b   Wawrzeńczyk, Czesław ^a  

^a WROC AW UNIVERSITY OF ENVIRONMENTAL AND LIFE SCIENCES   (Poland)

^b JAN KOCHANOWSKI UNIVERSITY   (Poland)

Author keywords

Enantioselective hydrolysis; Enzymatic resolution; Esterase; Lactones; Lipase

Indexed keywords

ENANTIOSELECTIVE HYDROLYSIS; ENZYMATIC RESOLUTION; ESTERASE; LACTONES;

ENANTIOMERS; ENANTIOSELECTIVITY; ENZYME ACTIVITY; HYDROLYSIS; LIPASES;

ESTERS;

5 (3 METHYLBUTYLIDENE) 4 METHYLTETRAHYDROFURAN 2 ONE; 5 (3,3 DIMETHYLBUTYLIDENE) 4 METHYLTETRAHYDROFURAN 2 ONE; GAMMA LACTONE DERIVATIVE; OXOACID; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; BURKHOLDERIA CEPACIA; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME SUBSTRATE; HYDROLYSIS; NONHUMAN; RHIZOPUS; RHIZOPUS ARRHIZUS; RHIZOPUS NIVEUS; SWINE;

RHIZOPUS NIVEUS; RHIZOPUS ORYZAE; SUS;

EID: 33947710731     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.1080/10242420601184044     Document Type: Article

References (22)

1. Azerad, R. (1995) Application of biocatalysts in organic synthesis. Bull Soc Chim Fr, 132, pp. 17-51.
2. Barrero, AF, Oltra, JE and Alvarez, M. (2000) A new strategy for the synthesis of (+)-vernolepin related compounds: An unusual sulfene elimination leads to the 2-oxa-cis-decalin skeleton. Tetrahedron Lett, 41, pp. 7639-7643.
3. Bauman, M., Hauer, BH and Bornscheuer, UT (2000) Rapid screening of hydrolases for the enantioselective conversion of 'difficult-to-resolve' substrates. Tetrahedron: Asymmetry, 11, pp. 4781-4790.
4. Blanco, L., Guibe-Jampel, E. and Rousseau, G. (1988) Enzymatic resolution of racemic lactones. Tetrahedron Lett, 29, pp. 1915-1918.
5. Brenna, E., Fuganti, C. and Serra, S. (2003) Enantioselective perception of chiral odorants. Tetrahedron: Asymmetry, 14, pp. 1-42.
6. Caro, Y.,Masaguer, ChF and Ravina, E. (2001) Synthesis of optically active β-benzyl-γ-butyrolactone through lipase-catalyzed kinetic resolution. Tetrahedron: Asymmetry, 1, pp. 1723-1726.
7. Enzelberger, M., Bornscheuer, UT, Gatfield, I. and Schmid, RD (1997) Lipase-catalysed resolution of γ- and δ-lactones. J Biotechnol, 56, pp. 129-133.
8. Gebbinck, E., Jansen, B. and Groot, A. (2002) Insect antifeedant activity of clerodane diterpenes and related model compounds. Phytochemistry, 61, pp. 737-707.
9. Kondaveti, L., Al-Azemi, TF and Bishut, K. (2002) Lipase-catalyzed solvent-free kinetic resolution of substituted racemic ε-caprolactones. Tetrahedron: Asymmetry, 13, pp. 129-135.
10. Leuenberger, HGW (1990) Biotransformation-a useful tool in organic chemistry. Pure Appl Chem, 62, pp. 753-768.
11. Mosandl, A. and Gunter, C. (1989) Stereoisomeric flavour compounds. 20.1. Structure and properties of γ-lactone enantiomers. J Agric Food Chem, 37, pp. 413-419.
12. Neerman, M. (2003) Sesquiterpene lactones: A diverse class of compounds found in essential oils possessing antibacterial and antifungal properties. Int J Aromatherapy, 13, pp. 114-120.
13. Olejniczak, T. and Ciunik, Z. (2004) Enantioselective hydrolysis of δ-acetoxy-γ-lactones. Tetrahedron: Asymmetry, 15, pp. 3743-3749.
14. Olejniczak, T.,Gawroński, J. and Wawrzeńczyk, C. (2001) Lactones 6. Microbial lactonization of γ,δ-epoxy esters. Chirality, 13, pp. 302-307.
15. Olejniczak, T., Grabarczyk, M., Nawrot, J. and Wawrzeńczyk, C. (2000) Laktony 10. Hydroksy-i acetoksylaktony terpenoidowe-syntetyczne deterenty pokarmowe owadów. W: Biotechnologia, 3, pp. 106-117.
16. Olejniczak, T., Nawrot, J., Ciunik, Z. and Wawrzenczyk, C. (2000) Lactones 5. Synthesis of some terpenoid lactones from γ,δ-epoxy esters. Polish J Chem, 74, pp. 673-680.
17. Pittaco, G., Santi, AS and Valentin, E. (2000) Enzymic resolution of α-methylene-β-lactonic ester. Tetrahedron: Asymmetry, 11, pp. 3263-3267.
18. Smith, DE and Coffmen, JR (1960) Analysis of food flavors by gas-liquid chromatography. Separation and identification of the natural components from bread pre-ferment liquid. Anal Chem, 32, pp. 1733-1737.
19. Wedge, DE, Galindo, JCG and Macias, FA (2000) Fungicidal activity of natural and synthetic sesquiterpene lactone analogs. Phytochemistry, 53, pp. 747-757.
20. Wzorek, A., Gibka, J., Kula, J. and Wawrzeńczyk, C. (2003) Nowy zapachowy lakton i sposób jego otrzymywania. Polish Pat. Appl.
21. Wzorek, A. and Wawrzeńczyk, C. (2003) Nowy nienasycony lakton terpenoidowy oraz sposób jego otrzymywania. Polish Pat. Appl.
22. Villeneuve, P., Muderhwa, JM, Grille, J. and Haas, MJ (2000) Customizing lipases for biocatalysis: A survey of chemical, physical and molecular biological approaches. J Mol Catal B: Enzymatic, 9, pp. 113-148.