Regioselective enzymatic procedure for preparing 3'-O-stearoyl-6-azauridine by using burkholderia cepacia Lipase

Biotechnology and Bioprocess Engineering

Volumn 17, Issue 2, 2012, Pages 393-397

  Wang, Zhao Yu ^a   Bi, Yan Hong ^a   Zong, Min Hua ^b  

^a HUAIYIN INSTITUTE OF TECHNOLOGY   (China)

^b SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

6 azauridine; Burkholderia cepacia lipase; Enzyme catalysis; Organic solvent; Regioselective acylation

Indexed keywords

6-AZAURIDINE; BURKHOLDERIA CEPACIA; ENZYME CATALYSIS; HYDROXYL GROUPS; MOLAR RATIO; PRODRUGS; REACTION SOLVENTS; REACTION TEMPERATURE; REGIO-SELECTIVE; REGIOSELECTIVE ACYLATION; SUBSTRATE CONVERSION; VINYL STEARATE;

ACETONE; ACYLATION; ORGANIC SOLVENTS; REACTION RATES;

REGIOSELECTIVITY;

3' 0 STEAROYL 6 AZAURIDINE; AZAURIDINE DERIVATIVE; ORGANIC SOLVENT; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; BURKHOLDERIA CEPACIA; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; ENZYME ACTIVITY; ENZYME STABILITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; REACTION TIME; RESPONSE TIME; TEMPERATURE;

BURKHOLDERIA CEPACIA;

EID: 84861081557     PISSN: 12268372     EISSN: 19763816     Source Type: Journal    
DOI: 10.1007/s12257-011-0483-y     Document Type: Article

References (26)

1. Pejanovi , V., V. Piperski, D. Uglje oei -Kilibarda, J. Tasi , M. Da evi , L. Medi -Mija evi , E. Guni , M. Popsavin, and V. Popsavin (2006) Synthesis and biological activity of some new 5'-O-acyl tiazofurin derivatives. Eur. J. Med. Chem. 41: 503-512.
2. Ferrero, M. and V. Gotor (2000) Biocatalytic selective modificationsof conventional nucleosides, carbocyclic nucleosides, and C-nucleosides. Chem. Rev. 100: 4319-4348.
3. Li, X. F., M. H. Zong, and G. L. Zhao (2010) Highly regioselectiveenzymatic synthesis of 5'-O-stearate of 1-β-D- arabinofuranosylcytosine in binary organic solvent mixtures. Appl. Microbiol. Biotechnol. 88: 1-7.
4. Wang, H., M. H. Zong, H. Wu, and W. Y. Lou (2007) Novel and highly regioselective route for synthesis of 5-fluorouridine lipophilic ester derivatives by lipozyme TL IM. J. Biotechnol. 129: 689-695. (Pubitemid 46590454)
5. Li, N., M. H. Zong, and D. Ma (2008) Regioselective acylation of nucleosides catalyzed by Candida Antarctica lipase B: Enzyme substrate recognition. Eur. J. Org. Chem. 2008: 5375-5378.
6. Li, N., M. H. Zong, and D. Ma (2009) Regioselective acylation of nucleosides and their analogs catalyzed by Pseudomonas cepacia lipase: Enzyme substrate recognition. Tetrahed. 65:1063-1068.
7. Clercq, E. De (2011) A 40-year journey in the antiviral drug field. Ann. R. Pharm. 51: 1-24.
8. Lum, P. Y., L. Y. Ngo, A. H. Bakken, and J. D. Unadkat (2000) Human intestinal es nucleoside transporter: Molecular characterization and nucleoside inhibitory profiles. Canc. Chemot. 45: 273-278. (Pubitemid 30151519)
9. Zeng, H., Z. P. Lin, and A. C. Sartorelli (2004) Resistance topurine and pyrimidine nucleoside and nucleobase analogs by the human MDR1 transfected murine leukemia cell line L1210/ VMDRC. 06. Biochem. Pharmacol. 68: 911-921. (Pubitemid 39044518)
10. Bello, A. M., D. Konforte, E. Poduch, C. Furlonger, L. Wei, Y.Liu, M. Lewis, E. F. Pai, C. J. Paige, and L. P. Kotra (2009) Structure- activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents. J. Med. Chem. 52: 1648-1658.
11. Plevová, J., F. H. Mohamed, and I. Jank (1971) Elimination of 2',3',5'-tri-O-acetyl-6-azauridine in the rat and in man. Biochem. Pharmacol. 20: 2079-2083.
12. Zinni, M. A., L. E. Iglesias, and A. M. Iribarren (2007) Preparation of potential 3-deazauridine and 6-azauridine prodrugs through an enzymatic alcoholysis. J. Mol. Catal. B-Enz. 47: 86-90. (Pubitemid 46824185)
13. Dáaz-Rodráguez, A., S. Fernández, Y. S. Sanghvi, M. Ferrero, and V. Gotor (2006) Novel chemoenzymatic protocol for the synthesis of 3-O-dimethoxytrityl-2-deoxynucleoside derivatives asbuilding blocks for oligonucleotide synthesis. Org. Process Res. Dev. 10: 581-587. (Pubitemid 44012701)
14. Wang, Z. Y., N. Li, and M. H. Zong (2009) A simple procedurefor the synthesis of potential 6-azauridine prodrugs by Thermomyces lanuginosus lipase. J. Mol. Catal. B-Enz. 59: 212-219.
15. Wang, Z. Y. and M. H. Zong (2009) Recognition of acyl donorsby lipase CAL-B in the acylation of 6-azauridine. Biotechnol. Prog. 25: 784-791.
16. Hamamura, E. K., M. Prystasz, J. P. H. Verheyden, J. G. Moffatt,K. Yamaguchi, N. Uchida, K. Sato, A. Nomura, and O. Shiratori (1976) Reactions of 2-acyloxyisobutyryl halides with nucleosides. 6. Synthesis and biological evaluation of some 3'-acyl derivatives of 2,2'-anhydro-1-(β-D- arabinofuranosyl) cytosinehydrochloride. J. Med. Chem. 19: 654-662.
17. Halling, P. J. (1994) Thermodynamic predictions for biocatalysisin nonconventional media: theory, tests, and recommendations for experimental design and analysis. Enz. Microb. Technol. 16: 178-206. (Pubitemid 24102654)
18. Bell, G., P. J. Halling, B. D. Moore, J. Partridge, and D. G. Rees (1995) Biocatalyst behaviour in low-water systems. Trends Biotechnol. 13: 468-473.
19. Kumar, V., V. S. Parmar, and S. V. Malhotra (2010) Structuralmodifications of nucleosides in ionic liquids. Biochimie. 92: 1260-1265.
20. Almarsson, O. and A. M. Klibanov (1996) Remarkable activationof enzymes in nonaqueous media by denaturing organic cosolvents. Biotechnol. Bioeng. 49: 87-92. (Pubitemid 26001494)
21. Tsikaris, V., M. Sakarellos-Daitsiotis, N. Theophanidis, C. Sakarellos, M. T. Cung, and M. Marraud (1991) Significance of bound residual water in the DMSO solution structure of stable peptide hydrates. J. Chem. Soc., Perkin Trans. 2. 9: 1353-1357.
22. Anthonsen, T. and B. H. Hoff (1998) Resolution of derivatives of 1, 2-propanediol with lipase B from Candida antarctica: Effectof substrate structure, medium, water activity and acyl donor on enantiomeric ratio. Chem. Phys. Lipids 93: 199-207. (Pubitemid 28383217)
23. Chamouleau, F., D. Coulon, M. Girardin, and M. Ghoul (2001)Influence of water activity and water content on sugar esters lipase-catalyzed synthesis in organic media. J. Mol. Catal. B-Enz. 11: 949-954. (Pubitemid 32114282)
24. Klibanov, A. M. (2001) Improving enzymes by using them inorganic solvents. Nature 409: 241-246. (Pubitemid 32144293)
25. Soares, C. M., V. H. Teixeira, and A. M. Baptista (2003) Proteinstructure and dynamics in nonaqueous solvents: INSIGHTS from molecular dynamics simulation studies. Biophys. J. 84: 1628-1641. (Pubitemid 36322927)
26. Weber, H. K., H. Weber, and R. J. Kazlauskas (1999) Watchinglipase- catalyzed acylations using (Pubitemid 29423368)