Lipase-catalyzed kinetic resolution of (±)-1-(2-furyl) ethanol in nonaqueous media

Chirality

Volumn 26, Issue 6, 2014, Pages 286-292

  Devendran, Saravanan ^a   Yadav, Ganapati D ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

1 (2 Furyl) ethanol; Candida antarctica lipase B; kinetic resolution; ordered bi bi mechanism; vinyl acetate

Indexed keywords

ACETIC ACID ETHYL ESTER; ACETIC ANHYDRIDE; ACRYLIC ACID RESIN; ALCOHOL; BUTYRIC ACID; CANDIDA ANTARCTICA LIPASE B; ESTER; HEPTANE; LAURIC ACID; LIPASE B; METHYL ACETATE; RHIZOMUCOR MIEHEI LIPASE; THERMOMYCES LANUGINOSUS LIPASE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; VINYL ACETATE; 1-(2-FURYL)ETHANOL; FUNGAL PROTEIN; FURAN DERIVATIVE; IMMOBILIZED ENZYME; LIPASE B, CANDIDA ANTARCTICA; NOVOZYME 435; SOLVENT;

ARTICLE; BATCH REACTOR; CANDIDA ANTARCTICA; CATALYST; CHEMICAL REACTION; DONOR; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME CHEMISTRY; ENZYME KINETICS; ENZYME STABILITY; LIPASE CATALYZED KINETIC RESOLUTION; NONHUMAN; NONLINEAR REGRESSION ANALYSIS; PRIORITY JOURNAL; RHIZOMUCOR MIEHEI; SCALE UP; THERMOMYCES LANUGINOSUS; ANALOGS AND DERIVATIVES; CANDIDA; CATALYSIS; CHEMISTRY; ENZYMOLOGY; KINETICS; RHIZOMUCOR; STEREOISOMERISM; TEMPERATURE; VIBRATION;

CANDIDA; CATALYSIS; ENZYMES, IMMOBILIZED; ETHANOL; FUNGAL PROTEINS; FURANS; KINETICS; LIPASE; RHIZOMUCOR; SOLVENTS; STEREOISOMERISM; TEMPERATURE; VIBRATION;

EID: 84901188885     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22317     Document Type: Article

References (43)

1. Pollard JD, Woodley JM,. Biocatalysis for pharmaceutical intermediate: the future is now. Trends Biotechnol 2006; 25: 66-73.
2. Yadav GD, Sajgure AD, Dhoot SB,. Enzyme catalysis in fine chemical and pharmaceutical industries. In:, Bhattacharya SK, editor. Enzyme mixtures and complex biosynthesis. Austin, TX: Landes Biosciences; 2007. pp 79-107.
3. Wohlgemuth R,. Biocatalysis-key to sustainable industrial chemistry. Curr Opin Biotechnol 2010; 21: 713-724.
4. Patel RN,. Microbial/enzymatic synthesis of chiral drug intermediates. Adv Appl Microbiol 1999; 43: 91-140.
5. Mahmoudian M,. Biocatalytic production of chiral pharmaceutical intermediates. Biocat Biotrans 2000; 18: 105-116.
6. Carvalho CCCR,. Enzymatic and whole cell catalysis: Finding new strategies for old processes. Biotechnol Adv 2011; 29: 75-83.
7. Fatima Y, Kansal H, Soni P, Banerjee UC,. Enantioselective reduction of aryl ketones using immobilized cells of Candida viswanathii. Process Biochem 2007; 42: 1412-1418.
8. Clapes P, Garrabou X,. Current trends in asymmetric synthesis with aldolases. Adv Synth Catal 2011; 353: 2263-2283.
9. Yadav GD, Devendran S,. Lipase catalyzed kinetic resolution of (±) 1-(1-naphthyl) ethanol under microwave irradiation. J Mol Catal B: Enzym 2012; 81: 58-65.
10. Campillo-Alvarado G, Tover-Miranda R,. Recent advances and applications of the lipolytic activity of Carica papaya latex. J Mol Catal B: Enzym 2013; 90: 49-60.
11. Mendes AA, Oliveira PC, de Castro HF,. Properties and biotechnological applications of porcine pancreatic lipase. J Mol Catal B: Enzym 2012; 78: 119-134.
12. Yadav GD, Devendran S,. Lipase catalyzed synthesis of cinnamyl acetate via transesterification in non-aqueous medium. Process Biochem 2012; 47: 496-502.
13. Cantone S, Hanefeld U, Basso A,. Biocatalysis in non-conventional media-ionic liquids, supercritical fluids and the gas phase. Green Chem 2007; 9: 954-971.
14. Shan M, O'Doherty AG,. De novo asymmetric syntheses of SL0101 and analogues via a palladium catalyzed glycosylation. Org Lett 2006; 8: 5149-5152.
15. Borisova AS, Guppi RS, Kim JH, Wu B, Penn HJ, Liu H, O'Doherty AG,. A de novo approach to synthesis of glycosylated methymycin analogues with structural and stereochemcial diversity. Org Lett 2010; 12: 5150-5153.
16. Zamojski A, Grynkiewicz G,. The total synthesis of carbohydrates. 1972-1980. In:, Simon J, editor. The total synthesis of natural products, vol. 6. New York: John Wiley & Sons; 1984. p 141-235.
17. Kobayashi Y, Kumar BG, Kurachi T, Acharya PH, Yamazaki T, Kitazume T,. Furan ring oxidation strategy for the synthesis of macroshelides A and B. J Org Chem 2001; 66: 2011-2018.
18. Fantin G, Fogagnolo M, Guerzoni ME, Medici A, Pedrini P, Poli S,. Stereochemical control in bakers yeast redox biotransformation of aryl methyl ketones and carbinols. J Org Chem 1994; 59: 924-925.
19. Li X, Wu X, Chen W, Hancock FE, King F, Xiao J,. Asymmetric transfer hydrogenation in water with a supported noyori-lkariya catalyst. Org Lett 2004; 6: 3321-3324.
20. Mamaghani M, Mahmoodi NO, Moghisseh AA, Pourmohamad L,. Synthesis and kinetic resolution of furyl substituted secondary carbinols by procine pancreatic lipase under solvent free conditions. J Iran Chem Soc 2008; 5: 238-243.
21. Ghanem A, Schurig V,. Lipase-catalyzed irreversible transesterification of 1-(2-furyl) ethanol using isopropenyl acetate. Chirality 2001; 13: 118-123.
22. Sontakke JB, Yadav GD,. Kinetic modeling and statistical optimization of lipase catalysed enantioselective resolution of (R,S)-2-pentanol. Ind Eng Chem Res 2011; 50: 12975-12983.
23. Yadav GD, Sivakumar P,. Enzyme-catalysed optical resolution of mandelic acid via R/S (±)-methyl mandelate in non-aqueous media. Biochem Eng J 2004; 19: 101-107.
24. Hoffmann I, Silva VD, Nascimento MG,. Enantioselective resolution of (RS) -1-phenyletanol catalysed by lipases immobilized in starch films. J Braz Chem Soc 2011; 22: 1559-1567.
25. Ema T, Maeno S, Takaya Y, Sakai T, Utaka M,. Kinetic resolution of racemic 2-substituted 3-cyclopenten-1-ols by lipase-catalyzed transesterifications: A rational strategy to improve enantioselectivity. J Org Chem 1996; 61: 8610-8616.
26. Geng B, Wang M, Qi W, Su R, He Z,. Cinnamyl acetate synthesis by lipase-catalyzed transesterification in a solvent-free system. Biotechnol Appl Biochem 2012; 59: 270-275.
27. Pilissao C, Carvalho PO, Nascimento MG,. Potential application of native lipases in the resolution of (RS)-phenylethylamine. J Braz Chem Soc 2010; 21: 973-977.
28. Dhake KP, Deshmukh KM, Wagh YS, Singhal RS, Bhanage BM,. Investigation of steapsin lipase for kinetic resolution of secondary alcohols and synthesis of valuable acetates in non aqueous medium. J Mol Catal B: Enzym 2012; 77: 15-23.
29. Silva JMR, Nascimento MG,. Chemoenzymatic epoxidation of citronellol catalysed by lipases. Process Biochem 2012; 47: 517-522
30. Pan S, Liu X, Xie Y, Yi Y, Li C, Yan Y, Liu Y,. Esterification activity and conformation studies of Burkholderia cepacia lipase in conventional organic solvent, ionic liquids and their co-solvent mixture media. Bioresour Technol 2010; 101: 9822-9824.
31. Yadav GD, Borkar IV,. Synthesis of n-butyl acetamide over immobilized lipase. J Chem Technol Biotechnol 2009; 84: 420-426.
32. Wilke CR, Chang P,. Correlation of diffusion coefficients in dilute solutions. AIChE J 1955; 1: 264-270.
33. Perry RH, Green DW,. Perry's chemical engineers' handbook. New York: McGraw-Hill; 1984.
34. Jin X, Liu B, Ni Z, Wu Q, Lin X,. A novel control of enzymatic enantioselectivity through the racemic temperature influenced by reaction media. Enzyme Microb Technol 2011; 48: 454-457.
35. Sakai T, Kawabata I, Kishimoto T, Ema T, Utaka M,. Enhancement of the enantioselectivity in lipase-catalyzed kinetic resolutions of 3-phenyl-2H-azirine-2-methanol by lowering the temperature to -40C. J Org Chem 1997; 62: 4906-4907.
36. Segel H,. Enzyme kinetics: Behaviour and analysis of rapid equilibrium and steady-state enzyme systems. New York: John Wiley & Sons; 1975. pp 309-319.
37. Krishna SH, Divakar S, Prapulla SG, Karanth NG,. Enzymatic synthesis of isoamyl acetate using immobilized lipase from Rhizomucor miehei. J Biotechnol 2001; 87: 193-201.
38. Yadav GD, Borkar IV,. Kinetic and mechanistic investigation of microwave-assisted lipase catalyzed synthesis of citronellyl acetate. Ind Eng Chem Res 2009; 48: 7915-7922.
39. Yadav GD, Trivedi AH,. Kinetic modeling of immobilized lipase catalyzed transesterificatin of n-octanol with vinyl acetate in nonaqueous media. Enzyme Microb Technol 2003; 32: 783-789.
40. Yadav GD, Devi KM,. Enzymatic synthesis of perlauric acid using Novozyme 435. Biochem Eng J 2002; 10: 93-101.
41. Hara P, Turcu MC, Sundell R, Tosa M, Paizs C, Irimie FD, Kanerva LT,. Lipase-catalyzed asymmetric acylation in the chemoenzymatic synthesis of furan-based alcohols. Tetrahedron Asymm 2013; 24: 142-150.
42. Kamihska J, Gornicka I, Sikora M, Gora J,. Preparation of homochiral (S)- and (R)-l-(2-furyl) ethanols by lipase-catalyzed transesterification. Tetrahedron Asymm 1996; 7: 907-910.
43. Hara P, Hanefeld U, Kanerva LT,. Sol-gels and cross-linked aggregates of lipase PS from Burkholderia cepacia and their application in dry organic solvents. J Mol Catal B: Enzym 2008; 50: 80-86.