Recombinant lipase from Candida rugosa for regioselective hydrolysis of peracetylated nucleosides. A comparison with commercial non-recombinant lipases

Biocatalysis and Biotransformation

Volumn 28, Issue 2, 2010, Pages 108-116

  Bavaro, Teodora ^a,d   Ubiali, Daniela ^a,d   Brocca, Stefania ^b,d   Rocchietti, Silvia ^c,d   Nieto, Ines ^c,d   Pregnolato, Massimo ^a,d   Lotti, Marina ^b,d   Terreni, Marco ^a,d  

^a UNIVERSITY OF PAVIA   (Italy)

^b UNIVERSITY OF MILANO BICOCCA   (Italy)

^c Innovate Biotechnology Srl ^*  (Italy)

^d Italian Biocatalysis Center   (Italy)

Author keywords

Immobilization; Lipase; Nucleosides; Regioselectivity

Indexed keywords

AGAROSE; CANDIDA RUGOSA; COMMERCIAL LIPASE; CYTIDINE; GOOD YIELD; IMMOBILIZATION; LIPASE FROM CANDIDA RUGOSA; PYRIMIDINE NUCLEOSIDES; REGIOSELECTIVE HYDROLYSIS; SEPABEADS;

ACETONITRILE; BIOMOLECULES; CELL IMMOBILIZATION; CHEMICAL STABILITY; HYDROLYSIS; REGIOSELECTIVITY;

LIPASES;

EUPERGIT; NUCLEOSIDE; RECOMBINANT ENZYME; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CANDIDA RUGOSA; CONTROLLED STUDY; DRUG STABILITY; DRUG SYNTHESIS; ENZYME IMMOBILIZATION; ENZYME SYNTHESIS; HYDROLYSIS; NONHUMAN; PICHIA PASTORIS;

CANDIDA RUGOSA;

EID: 77249101540     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.3109/10242420903497362     Document Type: Article

References (38)

1. Akoh CC, Lee GC, Shaw JF. 2004. Protein engineering and applications of Candida rugosa lipase isoforms. Lipids 39:513-526.
2. Bastida A, Sabuquillo P, Armisen P, Fernandez-Lafuente R, Huguet J, Guisan JM. 1998. A single step purification, immobilization, and hyperactivation of lipases via interfacial adsorption on strongly hydrophobic supports. Biotechnol Bioeng 58:486-493.
3. Bavaro T, Rocchietti S, Ubiali D, Filice M, Terreni M, Pregnolato M. 2009. A versatile synthesis of 5′-functionalized nucleosides through regioselective enzymatic hydrolysis of their peracetylated precursors. Eur J Org Chem 12:1967-1975.
4. Belle V, Fournel A, Woudstra M, Ranaldi S, Prieri F, Thome V, Currault J, Verger R, Guigliarelli B, Carriere F. 2007. Probing the opening of the pancreatic lipase lid using site-directed spin labeling and EPR spectroscopy. Biochemistry 46:2205-2214.
5. Bradford MM. 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254.
6. Brocca S, Grandori R, Breviario D, Lotti M. 1995. Localization of lipase genes on Candida rugosa chromosomes. Curr Genet 28:454S-457S.
7. Brocca S, Schmidt-Dannert C, Lotti M, Alberghina L, Schmid R. 1998. Design, total synthesis, and functional overexpression of the Candida rugosa lipl gene coding for a major industrial lipase. Protein Sci 7:1415-1422.
8. Brocca S, Secundo F, Ossola M, Alberghina L, Carrea G, Lotti M. 2003. Sequence of the lid affects activity and specificity of Candida rugosa lipase isoenzymes. Protein Sci 12:2312-2319.
9. Cao L. 2005. Carrier-bound immobilized enzymes: Principles, application and design. Weinheim: Wiley-VCH.
10. Dalmau E, Montesinos JL, Lotti M, Casas C. 2000. Effect of different carbon sources on lipase production by Candida rugosa. Enzyme Microb Technol 26:657-663.
11. Diczfalusy MA, Hellman U, Alexson SHE. 1997. Isolation of carboxylester lipase (CEL) isoenzymes from Candida rugosa and identification of the corresponding genes. Arch Biochem Biophys 348:1-8.
12. Eydoux J, De Caro F, Ferrato P, Boullanger D, Lafont R, Laugier F, Carriere A, De Caro A. 2007. Further biochemical characterization of human pancreatic lipase-related protein 2 expressed in yeast cells. J Lipid Res 48:1539-1549.
13. Ferrero M, Gotor V. 2000. Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides, and C-nucleosides. Chem Rev 100:4319-4347.
14. Grochulski P, Li Y, Schrag JD, Bouthillier F, Smith P, Harrison D, Rubin B, Cygler M. 1993. Insights into interfacial activation from an open structure of Candida rugosa lipase. J Biol Chem 268:12843-12847.
15. Hsu KH, Lee GC, Shaw JF. 2008. Promoter analysis and differential expression of the Candida rugosa lipase gene family in response to culture conditions. J Agric Food Chem 56: 1992-1998.
16. Jyonouchi H. 1994. Nucleotide actions on humoral immune responses. J Nutr 124:138S-143S.
17. Katchalski-Katzir E, Kraemer DM. 2000. EupergitR C, a carrier for immobilization of enzymes of industrial potential. J Mol Catal B: Enzym 10:157-176.
18. Kawaguchi Y, Honda H, Taniguchi-Morimura J, Iwasaki S. 1989. The codon CUG is read as serine in an asporogenic yeast Candida cylindracea. Nature 341:164-166.
19. Laemmli UK. 1970. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227:680-685.
20. Lee GC, Tang SJ, Sun KH, Shaw JF. 1999. Analysis of the gene family encoding lipases in Candida rugosa by competitive reverse transcription-PCR. Appl Environ Microbiol 65:3888-3895.
21. Longhi S, Fusetti F, Grandori R, Lotti M, Vanoni M, Alberghina L. 1992. Cloning and nucleotide sequences of two lipase genes from Candida cylindracea. Biochim Biophys Acta 1131:227-232.
22. Longley DB, Harkin DP, Johnston PG. 2003. 5-Fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer 3:330-338.
23. Lotti M, Grandori R, Fusetti F, Longhi S, Brocca S, Tramontano A, Alberghina L. 1993. Cloning and analysis of Candida cylindracea lipase sequences. Gene 124:45-55.
24. Lotti M, Monticelli S, Montesinos JL, Brocca S, Valero F, Lafuente J. 1998. Physiological control on the expression and secretion of Candida rugosa lipase. Chem Phys Lipids 93:143-148.
25. Mileto D, Brocca S, Lotti M, Takagi M, Alquati C, Alberghina L. 1998. Characterization of the C. rugosa lipase system and overexpression of the lip1 isoenzyme in a non-conventional yeast. Chem Phys Lipids 93:47-55.
26. Nieto I, Rocchietti S, Ubiali D, Speranza G, Morelli CF, Fuentes IE, Alcantara AR, Terreni M. 2005. Immobilization of different protein fractions from Rhizomucor miehei lipase crude extract. Enzymatic resolution of (R,S)-2-tetralol. Enzyme Microb Technol 37:514-520.
27. Perigaud C, Gosselin G, Imbach JL. 1992. Analogues as chemotherapeutic agents: a review. Nucleosides Nucleotides Nucleic Acids 11:903-945.
28. Pernas M, Lopez C, Rua ML, Hermoso J. 2001. Influence of the conformational flexibility on the kinetics and dimerisation process of two Candida rugosa lipase isoenzymes. FEBS Lett 501:87-91.
29. Pregnolato M, Terreni M, Ubiali D, Bavaro T. 2008. 2′,3′-Di- Oacyl-5-fluoronucleosides. PCT/IB2008/000482.
30. Roncaglia DI, Schmidt AM, Iglesias LE, Iribarren AM. 2001. A simple and efficient enzymatic procedure for the deprotection of two base labile chlorinated purine ribosides. Biotechnol Lett 23:1439-1443.
31. Rua ML, Diaz-Maurino T, Fernandez VM, Otero C, Ballesteros A. 1993. Purification and characterization of two distinct lipases from Candida cylindracea. Biochim Biophys Acta 1156:181-189.
32. Secundo F, Carrea G, Tarabiono C, Brocca S, Lotti M. 2004. Activity and enantioselectivity of wildtype and lid mutated Candida rugosa lipase isoform 1 in organic solvents. Biotechnol Bioeng 86:236-240.
33. Singh HK, Cote GL, Sikorski RS. 1993. Enzymatic regioselective deacylation of 2′,3′,5′-tri-O-acylribonucleosides: enzymatic synthesis of 2′,3′-di-O-acylribonucleosides. Tetrahedron Lett 34:5201-5204.
34. Tang SJ, Shaw JF, Sun KH, Sun GH, Chang TY, Lin CK, Lo YC, Lee GC. 2001. Recombinant expression and characterization of the Candida rugosa lip4 lipase in Pichia pastoris: comparison of glycosylation, activity and stability. Arch Biochem Biophys 387:93-98.
35. Toscano MD, Woycechowsky KJ, Hilvert D. 2007. Minimalist active-site redesign: teaching old enzymes new tricks. Angew Chem Int Ed 46:3212-3236.
36. Uemura A, Nozaki K, Yamashita J, Yasumoto M. 1989. Regioselective deprotection of 3′,5′-O-acylated pyrimidine nucleosides. Tetrahedron Lett 30:3819-3820.
37. Zinni MA, Schmidt A, Gallo M, Iglesias L, Iribarren A. 2000. A simple enzymatic preparation of 2′,3′-di-O-acetylnucleosides through a lipase catalyzed alcoholysis. Molecules 5:533-534.
38. Zinni MA, Rodriguez SD, Pontiggia RM, Montserrat JM, Iglesias LE, Iribarren AM. 2004. Enzymatic alcoholysis of 3′,5′-di-O-acetyl- 2′-deoxynucleosides. J Mol Catal B: Enzym 29: 129-132.