Two lipase-catalyzed sequential synthesis of drug derivatives in organic media

Enzyme and Microbial Technology

Volumn 43, Issue 4-5, 2008, Pages 375-380

  Liu, Bokai ^a   Qian, Xueqi ^a   Wu, Qi ^a   Lin, Xianfu ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Aza Markovnikov addition; Lipase; N Heterocycle; Promiscuity; Vinyl ester

Indexed keywords

AMINES; CATALYSIS; CHEMICAL REACTIONS; DRUG DELIVERY; DRUG DOSAGE; ESTERIFICATION; ESTERS; FOOD ADDITIVES; ORGANIC COMPOUNDS; ORGANIC SOLVENTS; RATE CONSTANTS; REACTION RATES;

AZA-MARKOVNIKOV ADDITION; CONTROL EXPERIMENTS; ENZYMATIC SYNTHESES; ENZYME SOURCES; LIPASE; LIPASE CATALYSIS; N-HETEROCYCLE; N-HETEROCYCLES; NEW STRATEGY; ORGANIC MEDIUM; PROMISCUITY; REACTION-RATE; SEQUENTIAL SYNTHESIS; VINYL ESTER; VINYL ESTERS;

CHEMOTHERAPY;

DIMETHYL SULFOXIDE; DRUG DERIVATIVE; ESTER DERIVATIVE; HETEROCYCLIC COMPOUND; ORGANIC SOLVENT; TRIACYLGLYCEROL LIPASE;

ACYLATION; ADDITION REACTION; ARTICLE; BIOCATALYST; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME SPECIFICITY; MUCOR; MUCOR JAVANICUS; NONHUMAN; SCREENING;

MUCOR JAVANICUS;

EID: 49549124732     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.enzmictec.2008.05.008     Document Type: Article

References (35)

1. Bertau M. Novel developments in biocatalytic organic chemistry. Curr Org Chem 6 (2002) 987-1014
2. Reetz M.T. Directed evolution of enantioselective enzymes for organic chemistry. Curr Opin Chem Biol 4 (2000) 68-73
3. Secundo F., and Carrea G. Optimization of hydrolase efficiency in organic solvents. Chem Eur J 9 (2003) 3194-3199
4. Behrouzian B., Dawson D., Buist P.H., and Shanklin J. Oxidation of chiral 9-fluorinated substrates by castor stearoyl-ACP Delta(9) desaturase yields novel products. Chem Commun 8 (2001) 765-766
5. Palmer D.R.J., Garrett J.B., Sharma V., Meganathan R., Babbitt P.C., and Gerlt J.A. Unexpected divergence of enzyme function and sequence: "N-acylamino acid racemase" is o-succinylbenzoate synthase. Biochemistry 38 (1999) 4252-4258
6. Mugford P.F., Magloire V.P., and Kazlauskas R.J. Unexpected subtilisin-catalyzed hydrolysis of a sulfinamide bond in preference to a carboxamide bond in N-acyl sulfinamides. J Am Chem Soc 127 (2005) 6536-6537
7. Cai Y., Sun X.F., Wang N., and Lin X.F. Alkaline protease from Bacillus subtilis catalyzed Michael addition of pyrimidine derivatives to alpha, beta-ethylenic compounds in organic media. Synthesis 5 (2004) 671-674
8. Cai Y., Yao S.P., Wu Q., and Lin X.F. Michael addition of imidazole with acrylates catalyzed by alkaline protease from Bacillus subtilis in organic media. Biotechnol Lett 26 (2004) 525-528
9. Cai Y., Wu Q., Xiao Y.M., Lv D.S., and Lin X.F. Hydrolase-catalyzed Michael addition of imidazoles to acrylic monomers in organic medium. J Biotechnol 121 (2006) 330-337
10. Yao S.P., Lv D.S., Wu Q., Cai Y., Xu S.H., and Lin X.F. A single-enzyme, two-step, one-pot synthesis of N-substituted imidazole derivatives containing a glucose branch via combined acylation/Michael addition reaction. Chem Commun 17 (2004) 2006-2007
11. Wu W.B., Wang N., Xu J.M., Wu Q., and Lin X.F. Penicillin G acylase catalyzed Markovnikov addition of allopurinol to vinyl ester. Chem Commun 18 (2005) 2348-2350
12. Wu W.B., Xu J.M., Wu Q., Lv D.S., and Lin X.F. D-aminoacylase-catalyzed Markovnikov addition of azoles to vinyl esters in organic solvents. Synlett 16 (2005) 2433-2436
13. Wu W.B., Xu J.M., Wu Q., Lv D.S., and Lin X.F. Promiscuous acylases-catalyzed Markovnikov addition of N-heterocycles to vinyl esters in organic media. Adv Synth Catal 348 (2006) 487-492
14. Qian C., Xu J.M., Wu Q., Lv D.S., and Lin X.F. Promiscuous acylase-catalyzed aza-Michael additions of aromatic N-heterocycles in organic solvent. Tetrahedron Lett 48 (2007) 6100-6104
15. Xu J.M., Zhang F., Liu B.K., Wu Q., and Lin X.F. Promiscuous zinc-dependent acylase-mediated carbon-carbon bond formation in organic media. Chem Commun 20 (2007) 2078-2080
16. Ollis D.L., Cheah E., Cygler M., Dijkstra B., Frolow F., Franken S.M., Harel M., Remington S.J., Silman I., Schrag J., Sussman J.L., Verschueren K.H.G., and Goldman A. The alpha/beta-hydrolase fold. Protein Eng 5 (1992) 197-211
17. Holmquist M. Alpha/beta-hydrolase fold enzymes: Structures, functions and mechanisms. Curr Protein Pept Sci 1 (2000) 209-235
18. Kitazume T., Ikeya T., and Murata K. Synthesis of optically active trifluorinated compounds: asymmetric Michael addition with hydrolytic enzymes. J Chem Soc Chem Commun 17 (1986) 1331-1333
19. Branneby C., Carlqvist P., Magnusson A., Hult K., Brinck T., and Berglund P. Carbon-Carbon bonds by hydrolytic enzymes. J Am Chem Soc 125 (2003) 874-875
20. Branneby C., Carlqvist P., Hult K., Brinck T., and Berglund P. Aldol additions with mutant lipase: analysis by experiments and theoretical calculations. J Mol Catal B: Enzym 31 (2004) 123-128
21. Svedendahl M., Hult K., and Berglund P. Fast carbon-carbon bond formation by a promiscuous lipase. J Am Chem Soc 127 (2005) 17988-17989
22. Xu J.M., Yao S.P., Wu W.B., Lv D.S., and Lin X.F. Two-step sequential synthesis of pyrimidine derivatives containing a sugar branch via combining of enzymatic Michael addition/acylation. J Mol Catal B: Enzym 35 (2005) 122-127
23. Torre O., Alfonso I., and Gotor V. Lipase catalysed Michael addition of secondary amines to acrylonitrile. Chem Commun 15 (2004) 1724-1725
24. Bornscheuer U.T., and Kazlauskas R.J. Catalytic promiscuity in biocatalysis: Using old enzymes to form new bonds and follow new pathways. Angew Chem Int Ed 43 (2004) 6032-6040
25. Hult K., and Berglund P. Enzyme promiscuity: mechanism and applications. Trends Biotechnol 25 (2007) 231-238
26. Watanabea K., and Ueji S. Dimethyl sulfoxide as a co-solvent dramatically enhances the enantioselectivity in lipase-catalysed resolutions of 2-phenoxypropionic acyl derivatives. J Chem Soc-Perkin Trans 1 12 (2001) 1386-1390
27. Yokochi T., and Robertson K.D. Dimethyl sulfoxide stimulates the catalytic activity of de novo DNA methyltransferase 3a (Dnmt3a) in vitro. Bioorganic Chem 32 (2004) 234-243
28. Yang Z.R.W., Tendian S.W., Carson W.M., Brouillette W.J., Delucas L.J., and Brouillette C.G. Dimethyl sulfoxide at 2.5% (v/v) alters the structural cooperativity and unfolding mechanism of dimeric bacterial NAD(+) synthetase. Protein Sci 13 (2004) 830-841
29. Sehgal A.C., Tompson R., Cavanagh J., and Kelly R.M. Structural and catalytic response to temperature and cosolvents of carboxylesterase EST1 from the extremely thermoacidophilic archaeon Sulfolobus solfataricus P1. Biotechnol Bioeng 80 (2002) 784-793
30. Gotor-Fernandez V., Busto E., and Gotor V. Candida antarctica lipase B: an ideal biocatalyst for the preparation of nitrogenated organic compounds. Adv Synth Catal 348 (2006) 797-812
31. Azim H., Dekhterman A., Jiang Z.Z., and Gross R.A. Candida antarctica lipase b-catalyzed synthesis of poly(butylene succinate): Shorter chain building blocks also work. Biomacromolecules 7 (2006) 3093-3097
32. Ganske F., and Bornscheuer U.T. Lipase-catalyzed glucose fatty acid ester synthesis in ionic liquids. Org Lett 7 (2005) 3097-3098
33. Liu B.K., Wang N., Chen Z.C., Wu Q., and Lin X.F. Markedly enhancing lipase-catalyzed synthesis of nucleoside drugs' ester by using a mixture system containing organic solvents and ionic liquid. Bioorg Med Chem Lett 16 (2006) 3769-3771
34. Liu B.K., Wu Q., Xu J.M., and Lin X.F. N-Methylimidazole significantly improves lipase-catalysed acylation of ribavirin. Chem Commun 3 (2007) 295-297
35. 13C nuclear magnetic resonance spectra of O-acylglucose. Additivity of shift parameters and its application to structure elucidations. Chem Pharm Bull 28 (1980) 2065-2207