Resolution of N-hydroxymethyl vince lactam catalyzed by lipase in organic solvent

Journal of Chemical Technology and Biotechnology

Volumn 88, Issue 5, 2013, Pages 904-909

  Xun, Erna ^a,b   Wang, Jiaxin ^a   Zhang, Hong ^a   Chen, Ge ^a   Yue, Hong ^a   Zhao, Jimin ^b   Wang, Lei ^a   Wang, Zhi ^a  

^a JILIN UNIVERSITY   (China)

^b CHANGCHUN NORMAL UNIVERSITY   (China)

Author keywords

Lipase; N hydroxymethyl vince lactam; Organic solvent; Resolution

Indexed keywords

ENANTIOMERIC PURITY; ENANTIOSELECTIVE TRANSESTERIFICATION; ENZYMATIC RESOLUTIONS; MUCOR MIEHEI LIPASE; N-HYDROXYMETHYL VINCE LACTAM; OPTIMUM CONDITIONS; REACTION CONDITIONS; SINGLE ENANTIOMERS;

CATALYSIS; ENANTIOMERS; ENANTIOSELECTIVITY; INDUSTRIAL APPLICATIONS; METHANOL; OPTICAL RESOLVING POWER; ORGANIC SOLVENTS;

LIPASES;

LACTAM DERIVATIVE; N HYDROXYMETHYL VINCE LACTAM; ORGANIC SOLVENT; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONTROLLED STUDY; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME SPECIFICITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MUCOR; MUCOR MIEHEI; NONHUMAN; REACTION TIME; TRANSESTERIFICATION;

RHIZOMUCOR MIEHEI;

EID: 84876343831     PISSN: 02682575     EISSN: 10974660     Source Type: Journal    
DOI: 10.1002/jctb.3919     Document Type: Article

References (35)

1. Vince R Hua M, Synthesis and anti-HIV activity of carbocyclic 2', 3′-didehydro-2', 3′-dideoxy 2, 6-disubstituted purine nucleosides. J Med Chem 33: 17-21 (1990).
2. Taylor SJC, McCague R, Wisdom R, Lee C, Dickson K, Ruecroft G, et al, Development of the biocatalytic resolution of 2-azabicyclo [2.2.1] hept-5-en-3-one as an entry to single-enantiomer carbocyclic nucleosides. Tetrahedron: Asymmetry 4: 1117-1128 (1993).
3. Holt-Tiffin KE, (+)-and (-)-2-Azabicyclo [2.2.1] hept-5-en-3-one: extremely useful synthons. Chem Today 27: 23-25 (2009).
4. Taylor SJC, Sutherland AG, Lee C, Wisdom R, Thomas S, Roberts SM, et al, Chemoenzymatic synthesis of (-)-carbovir utilizing a whole cell catalyzed resolution of 2-azabicyclo [2.2.1] hept-5-en-3-one. J Chem Soc Chem Commun 16: 1120-1121 (1990).
5. Brabban AD, Littlechild J Wisdom R, Stereospecific γ-lactamase activity in a Pseudomonas fluorescens species. J Ind Microbiol 16: 8-14 (1996).
6. Taylor SJC, Brown RC, Keene PA Taylor IN, Novel screening methods-the key to cloning commercially successful biocatalysts. Bioorg Med Chem 7: 2163-2168 (1999).
7. Toogood HS, Brown RC, Line K, Keene PA, Taylor SJC, McCague R, et al, The use of a thermo-stable signature amidase in the resolution of the bicyclic synthon (rac)-[gamma]-lactam. Tetrahedron 60: 711-716 (2004).
8. Torres LL, Schließmann A, Schmidt M, Silva-Martin N, Hermoso JA, Berenguer J, et al, Promiscuous enantioselective (-)-γ-lactamase activity in the Pseudomonas fluorescens esterase I. Org Biomol Chem 10: 3388-3392 (2012).
9. Karl-Erich J Thorsten E, Lipases for biotechnology. Curr Opin Biotechnol 13: 390-397 (2002).
10. Nakano H, lwasa K, Okuyanm Y Hongo H, Lipase-catalyzed resolution of 2-azabicydo [2.2.1] hept-5-en-3-ones. Tetrahedron: Asymmetry 7: 2381-2386 (1996).
11. Shah S, Sharma S Gupta MN, Enzymatic transesterification for biodiesel production. Indian J Biochem Bio 40: 392-399 (2003).
12. Yaqoob M, Nabi A Masoom-Yasinzai M, Enzymatic transesterification between sugar alcohol and oils. J Chem Soc Pakistan 19: 210-213 (1997).
13. Santaniello E, Ferraboschi P Grisenti P, Lipase-catalyzed transesterification in organic solvents: application to the preparation of enantiomerically pure compounds. Enzyme Microbiol Technol 15: 367-382 (1993).
14. Ericsson DJ, Kasrayan A, Johansson P, Bergfors T, Sandström AG, Bäckvall JE, et al, X-ray structure of Candida antarctica lipase A shows a novel lid structure and a likely mode of interfacial activation. J Mol Biol 376: 109-119 (2008).
15. Shau-Wei T Pei-Yun W, Modification of enzyme surface negative charges via covalent immobilization for tailoring the activity and enantioselectivity. J Taiwan Institute Chem Eng 40: 364-370 (2009).
16. Garcia-Galan C, Berenguer-Murcia A, Fernández-Lafuente R Rodrigues RC, Potential of different enzyme immobilization strategies to improve enzyme performance. Adv Synth Catal 353: 2885-2904 (2011).
17. Cowan DA Fernández-Lafuente R, Enhancing the functional properties of thermophilic enzymes by chemical modification and immobilization. Enzyme Microbiol Technol 49: 326-346 (2011).
18. Mateo C, Palomo JM, Fernández-Lorente G, Guisán JM Fernández-Lafuente R, Improvement of enzyme activity, stability and selectivity via immobilization techniques. Enzyme Microbiol Technol 40: 1451-1463 (2007).
19. Rodrigues RC, Berenguer-Murcia Á Fernández-Lafuente R, Coupling chemical modification and immobilization to improve the catalytic performance of enzyme. Adv Synth Catal 353: 2216-2238 (2011).
20. Ganapati DY Archana HT, Kinetic modeling of immobilized-lipase catalyzed transesterification of n-octanol with vinyl acetate in non-aqueous media. Enzyme Microbiol Technol 32: 783-789 (2003).
21. Chen CS, Fujimoto Y, Girdaukas G Sih CJ, Quantitative analyses of biochemical kinetic resolutions of enantiomers. J Am Chem Soc 104: 7294-7299 (1982).
22. Shah S Gupta MN, Lipase catalyzed preparation of biodiesel from jatropha oil in a solvent free system. Process Biochem 42: 409-414 (2007).
23. Won K, Hong JK, Kim KJ Moon SJ, Lipase catalyzed enantioselective esterification of racemic ibuprofen coupled with pervaporation. Process Biochem 41: 264-269 (2006).
24. Lilin L, Wei D, Dehua L, Li W Zebo L, Lipase-catalyzed transesterification of rapeseed oils for biodiesel production with a novel organic solvent as reaction medium. J Mol Catal B-Enzyme 43: 58-62 (2006).
25. Ema T, Maeno S, Takaya Y, Sakai T Utaka M, Significant effect of acyl groups on enantioselectivity in lipase catalyzed transesterifications. Tetrahedron 7: 625-628 (1996).
26. Wu JY Liu SW, Influence of alcohol concentration on lipase catalyzed enantioselective esterification of racemic naproxen in isooctane: under controlled water activity. Enz Microbiol Technolnol 26: 124-130 (2000).
27. Laane C, Boeren S, Vos K Veeger C, Rules for optimization of biocatalysis in organic solvents. Biotechnol Bioeng 30: 81-87 (1987).
28. Gorman LAS Dordick JS, Organic solvents strip water off enzymes. Biotechnol Bioeng 39: 392-397 (1992).
29. Serdakowski AL Dordick JS, Enzyme activation for organic solvents made easy. Trends Biotechnol 26: 48-54 (2008).
30. Bai S, Guo Z, Liu W Sun Y, Resolution of (±)-menthol by immobilized Candida rugosa lipase on superparamagnetic nanoparticles. Food Chem 96: 1-7 (2006).
31. Phillips RS, Temperature modulation of the stereochemistry of enzymatic catalysis: prospects for exploitation. Trends Biotechnol 14: 13-16 (1996).
32. Wehtje E, Costes D Adlercreutz P, Enantioselectivity of lipases: effects of water activity. J Mol Catal B-Enzyme 3: 221-230 (1997).
33. Nirprit SD Jagdeep K, Immobilization, stability and esterification studies of a lipase from a Bacillus sp. Biotechnol Appl Biochem 36: 7-12 (2002).
34. Halling PJ, Organic liquids and biocatalysts: theory and practice. Trends biotechnol 7: 50-52 (1989).
35. Ghamgui H, Karra-Chaabouni M, Bezzine S, Miled N Gargouri Y, Production of isoamyl acetate with immobilized Staphylococcus simulans lipase in a solvent-free system. Enz Microbiol Technol 38: 788-794 (2006).