Combining regio- and enantioselectivity of lipases for the preparation of (R)-4-chloro-2-butanol

Chirality

Volumn 19, Issue 1, 2007, Pages 44-50

  Méndez, Jonh J ^a,b   Oromi, Mireia ^a   Cervero, Maria ^a   Balcelis, Mercè ^a   Torres, Mercè ^a   Canela, Ramon ^a  

^a UNIVERSITY OF LLEIDA   (Spain)

^b UNIVERSIDAD DEL TOLIMA   (Colombia)

Author keywords

Biocatalyst; Chlorohydrin esters; Enantiomer; Optical resolution; Resting cells

Indexed keywords

2 BUTANOL; 4 CHLORO 2 BUTANOL; CARBOXYLIC ACID DERIVATIVE; CHLOROHYDRIN DERIVATIVE; ESTER; FUNGAL ENZYME; TRIACYLGLYCEROL LIPASE;

ARTICLE; ASPERGILLUS FLAVUS; BIOCATALYST; CANDIDA; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; ENZYME ACTIVITY; FENNEL; GAS CHROMATOGRAPHY; HYDROLYSIS; NONHUMAN; PLANT SEED; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RHIZOPUS ORYZAE; SUNFLOWER; TEMPERATURE;

EID: 33845562416     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20339     Document Type: Article

References (26)

1. Zuegg J, Honig H, Schrag JD, Cygler M. Selectivity of lipases: conformational analysis of suggested intermediates in ester hydrolysis of chiral primary and secondary alcohols. J Mol Catal B 1997;3: 83-98.
2. Koeller KM, Wong CH. Enzymes for chemical synthesis. Nature 2001;409:232-240.
3. Balcao VM, Paiva AL, Malcata FX. Bioreactors with immobilized lipases: State of the art. Enzyme Microb Technol 1996;18:392-416.
4. Ghanem A, Aboul-Enein HY. Application of lipases in kinetic resolution of racemates. Chirality 2005;17:1-15.
5. Faber K. Biotransformation in Organic Chemistry. Berlin: Springer-Verlag; 1992.
6. Bornscheuer UT. Trends and challenges in enzyme technology. In: Scheper T, editors. Biotechnology for the future. Advances in Biochemical Engineering/Biotechnology, Berlin: Springer-Verlag; 2005. Vol 100. p 181-203.
7. Kvittingen L. Some aspects of biocatalysis in organic solvents. Tetrahedron 1994;50:8253-8274.
8. Villeneuve P, Muderhwa JM, Graille J, Haas MJ. Customizing lipases for biocatalysis: A survey of chemical, physical and molecular biological approaches. J Mol Catal B 2000;9:113-148.
9. Powell KA, Ramer SW, del Cardayré SB, Stemmer WPC, Tobin MB, Longchamp PF, Huisman GW. Directed evolution and biocatalysis. Angew Chem Int Ed 2001;40:3948-3859.
10. Najera C, Yus M, Seebach D. C-metallated chiral alkoxides as D-2-reagent and D-3-reagent for the synthesis of enantiomerically pure compounds (Epc-synthesis). Helv Chim Acta 1984;67:289-300.
11. Torres M, Méndez JJ, Sanahuja V, Canela R. Reactive extraction of the acylglycerides present in various material using Rhizopus oryzae resting cells. Biocatal Biotransform 2003;21:129-134.
12. Meltzer RI, King JA. The mode of addition of a Grignard reagent to an aryl allyl ether. J Am Chem Soc 1953;75:1355-1359.
13. Méndez JJ, Eras J, Balcells M, Canela R. Influence of carboxylic acids on the synthesis of chlorohydrin esters from 1,3-butanediol. Synth Commun 2006;36:1167-1175.
14. Eras J, Méndez JJ, Balcells M, Canela R. Chlorotrimethylsilane: A suitable reagent for the synthesis of chlorohydrin esters. J Org Chem 2002;67:8631-8634.
15. Wilen SH, Delguzzo L, Saferstein R. Experimental evidence for AcO-7 neighboring group participation. Tetrahedron 1987;43:5089-5094.
16. Miller JJ. Cleavage of 1,3-butanediol cyclic sulfate with hydrogen chloride. J Org Chem 1962;27:2680-2681.
17. Rakels JLL, Straathof AJJ, Heijnen JJ. A simple method to determine the enantiomeric ratio in enantioselective biocatalysis. Enzyme Microb Technol 1993;15:1051-1056.
18. Wescott CR, Klibanov AM. The solvent dependence of enzyme specificity. Biochim Biophys Acta 1994;1206:1-9.
19. Klibanov AM. Improving enzymes by using them in organic solvents. Nature 2001;409:241-246.
20. Klibanov AM. Asymmetric transformations catalyzed by enzymes in organic solvents. Acc Chem Res 1990;23:114-120.
21. Zaks A, Klibanov AM. Enzymatic catalysis in nonaqueous solvents. J Biol Chem 1988;263:3194-3201.
22. Laane C, Boeren S, Vos K, Veeger C. Rules for optimization of biocatalysis in organic solvents. Biotechnol Bioeng 1987;30:81-87.
23. Hirose Y, Kariya K, Sasaki I, Kurono Y, Ebiike H, Achiwa K. Drastic solvent effect on lipase-catalyzed enantioselective hydrolysis of prochiral 1,4-dihydropyridines. Tetrahedron Lett 1992;33:7157-7160.
24. Faber K. Biotransformations of non-natural compounds: State of the art and future development. Pure Appl Chem 1997;69:1613-1632.
25. Phillips RS. Temperature modulation of the stereochemistry of enzymatic catalysis: Prospects for exploitation. Trends Biotechnol 1996;14:13-16.
26. Heinsman NWJT, Franssen MCR, Van der Padt A, Boom RM, Van't Riet K, de Groot A. Lipase-mediated resolution of branched chain fatty acids. Biocatal Biotransform 2002;20:297-309.