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Original Articles

Controllable Regioselective Acylation of Flavonoids Catalyzed by Lipase in Microreactors

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Pages 450-462 | Received 27 Dec 2012, Accepted 07 Sep 2013, Published online: 11 Oct 2013

REFERENCES

  • Saleh , M. M. , Hashem , F. A. and Glombitza , K. W. 1998 . Study of Citrus taitensis and radical scavenger activity of the flavonoids isolated . Food Chem. , 63 : 397 – 400 .
  • Sakihama , Y. , Cohen , M. F. , Grace , S. C. and Yamasaki , H. 2002 . Plant phenolic antioxidant and prooxidant activities: phenolics-induced oxidative damage mediated by metals in plants . Toxicology , 177 : 67 – 80 .
  • Ferguson , P. J. , Kurowska , E. D. , Freeman , J. A. , Chambers , F. and Koropatnick , D. J. 2004 . A flavonoid fraction from cranberry extract inhibits proliferation of human tumor cell lines . J. Nutr. , 134 : 1529 – 1535 .
  • Lagiou , P. , Samoli , E. , Lagiou , A. , Tzonou , A. , Kalandidi , A. , Peterson , J. , Dwyer , J. and Trichopoulos , D. 2004 . Intake of specific flavonoid classes and coronary heart disease-a case-control study in Greece . Eur. J. Clin. Nutr. , 58 : 1643 – 1648 .
  • Mozhaev , V. V. , Budde , C. L. , Rich , J. O. , Usyatinsky , A. Y. , Michels , P. C. , Khmelnitsky , Y. L. , Clark , D. S. and Dordick , J. S. 1998 . Regioselective enzymatic acylation as a tool for producing solution-phase combinatorial libraries . Tetrahedron , 54 : 3971 – 3982 .
  • Ardhaoui , M. , Falcimaigne , A. , Engasser , J. M. , Moussou , P. , Pauly , G. and Ghoul , M. 2004 . Acylation of natural flavonoids using lipase of candida antarctica as biocatalyst . J. Mol. Catal. B-Enzym. , 29 : 63 – 67 .
  • Enaud , E. , Humeau , C. , Piffaut , B. and Girardin , M. 2004 . Enzymatic synthesis of new aromatic esters of phloridzin . J. Mol. Catal. B Enzym. , 27 : 1 – 6 .
  • Nakajima , N. , Ishihara , K. , Itoh , T. , Furuya , T. and Hamada , H. 1999 . Lipase-catalyzed direct and regioselective acylation of flavonoid glucoside for mechanistic investigation of stable plant pigments . J. Biosci. Bioeng. , 87 : 105 – 107 .
  • Gayot , S. , Santarelli , X. and Coulon , D. 2003 . Modification of flavonoid using lipase in non-conventional media: effect of the water content . J. Biotechnol , 101 : 29 – 36 .
  • Gao , C. L. , Mayon , P. , MacManus , D. A. and Vulfson , E. N. 2000 . Novel enzymatic approach to the synthesis of flavonoid glycosides and their esters . Biotechnol. Bioeng. , 71 : 235 – 243 .
  • Passicos , E. , Santarelli , X. and Coulon , D. 2004 . Regioselective acylation of flavonoids catalyzed by immobilized Candida antarctica lipase under reduced pressure . Biotechnol. Lett. , 26 : 1073 – 1076 .
  • Kontogianni , A. , Skouridou , V. , Sereti , V. , Stamatis , H. and Kolisis , F. N. 2003 . Lipase-catalyzed esterification of rutin and naringin with fatty acids of medium carbon chain . J. Molec. Catal. B Enzym. , 21 : 59 – 62 .
  • Kontogianni , A. , Skouridou , V. , Sereti , V. , Stamatis , H. and Kolisis , F. N. 2001 . Regioselective acylation of flavonoids catalyzed by lipase in low toxicity media . Eur. J. Lipid Sci. Technol. , 103 : 655 – 660 .
  • Fernandes , P. 2010 . Miniaturization in biocatalysis . Int. J. Mol. Sci. , 11 : 858 – 879 .
  • Mason , B. P. , Price , K. E. , Steinbacher , J. L. , Bogdan , A. R. and McQuade , D. T. 2007 . Greener approaches to organic synthesis using microreactor technology . Chem. Rev. , 107 : 2300 – 2318 .
  • Miller , P. W. , Long , N. J. , Mello , A. J. , Vilar , R. , Passchier , J. and Gee , A. 2006 . Rapid formation of amides via carbonylative coupling reactions using a microfluidic device . Chem. Commun. , 5 : 546 – 548 .
  • Miyazaki , M. and Maeda , H. 2006 . Microchannel enzyme reactors and their applications for processing . Trends Biotechnol. , 24 : 463 – 470 .
  • Nagaki , A. , Takabayashi , N. , Tomida , Y. and Yoshida , J. 2008 . Selective monolithiation of dibromobiaryls using microflow systems . Org. Lett. , 10 : 3937 – 3940 .
  • Nagaki , A. , Kim , H. and Yoshida , J. 2008 . Aryllithium compounds bearing alkoxycarbonyl groups: generation and reactions using a microflow system . Angew. Chem. Int. Ed. , 47 : 7833 – 7835 .
  • Patil , D. R. , Rethwisch , D. G. and Dordick , J. S. 1991 . Enzymatic synthesis of a sucrose-containing linear polyester in nearly anhydrous organic media . Biotechnol. Bioeng. , 37 : 639 – 646 .
  • Schoemaker , H. E. , Mink , D. and Wubbolts , M. G. 2003 . Dispelling the myths-biocatalysis in industrial synthesis . Science , 299 : 1694 – 1670 .
  • Belder , D. , Ludwig , M. , Wang , L. W. and Reetz , M. T. 2006 . Enantioselective catalysis and analysis on a chip . Angew. Chem. Int. Ed. , 45 : 2463 – 2466 .
  • Doku , G. N. , Verboom , W. , Reinhoudt , D. N. and Vandenberg , A. 2005 . On-microchip multiphase chemistry-a review of microreactor design principles and reagent contacting modes . Tetrahedron , 61 : 2733
  • Ferrer , M. , Cruces , M. A. , Bernabeá , M. , Ballesteros , A. and Plou , F. J. 1999 . Lipase-catalyzed regioselective acylation of sucrose in two-solvent mixtures . Biotechnol. Bioeng. , 65 : 10 – 16 .
  • Ganske , F. and Bornscheuer , U. T. 2005 . Optimization of lipase-catalyzed glucose fatty acid ester synthesis in a two-phase system containing ionic liquids and t-BuOH . J. Mol. Catal. B Enzym. , 36 : 40 – 46 .
  • Geyer , K. , Codee , J. D.C. and Seeberger , P. H. 2006 . Microreactors as tools for synthetic chemists-the chemists’ round-bottomed flask of the 21st century? . Chem. Eur. J. , 12 : 8434 – 8438 .
  • Hessel , V. and Lowe , H. 2005 . Organic synthesis with microstructured reactors . Chem. Eng. Tech. , 28 : 267 – 284 .
  • Honda , T. , Miyazaki , M. , Nakamura , H. and Maeda , H. 2005 . Immobilization of enzymes on a microchannel surface through cross-linking polymerization . Chem. Commun. , 40 : 5062 – 5064 .
  • Kanno , K. , Kawazumi , H. , Miyazaki , M. , Maeda , H. and Fujii , M. 2002 . Enhanced enzymatic reactions in a microchannel reactor . Aust. J. Chem. , 55 : 687 – 690 .
  • Kanno , K. , Maeda , H. , Izumo , S. , Ikuno , M. , Takeshita , K. , Tashiro , A. and Fujii , M. 2002 . Rapid enzymatic transglycosylation and oligosaccharide synthesis in a microchip reactor . Lab Chip , 2 : 15 – 19 .
  • Kirschning , A. , Monenschein , H. and Wittenberg , R. 2001 . Functionalized polymers-emerging versatile tools for solution-phase chemistry and automated parallel synthesis . Angew. Chem. Int. Ed. , 40 : 650 – 679 .
  • Krenkova , J. and Foret , F. 2004 . Immobilized microfluidic enzymatic reactors . Electrophoresis , 25 : 3550 – 3563 .
  • Du , L. H. and Luo , X. P. 2012 . Lipase-catalyzed regioselective acylation of sugar in microreactors . Rsc. Adv. , 2 : 2663 – 2665 .

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