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Volumn 118, Issue , 2012, Pages 82-88

Regioselective enzymatic undecylenoylation of 8-chloroadenosine and its analogs with biomass-based 2-methyltetrahydrofuran as solvent

Author keywords

2 Methyltetrahydrofuran; Acylation; Enzyme substrate recognition; Lipase from Penicillium expansum; Purine nucleosides

Indexed keywords

2-METHYLTETRAHYDROFURAN; BIOCATALYSIS; BIOCATALYTIC PROCESS; COSOLVENTS; ENZYMATIC ACYLATION; ENZYME DOSAGE; ENZYME SUBSTRATES; HIGH YIELD; LIPASE-CATALYZED; MOLAR RATIO; OPTIMUM REACTION; ORGANOMETALLIC REACTION; PENICILLIUM EXPANSUM; PURINE NUCLEOSIDES; REACTION TEMPERATURE; REGIO-SELECTIVE; REGIOSELECTIVE ACYLATION; UNDECYLENIC ACID;

EID: 84862238642     PISSN: 09608524     EISSN: 18732976     Source Type: Journal    
DOI: 10.1016/j.biortech.2012.04.104     Document Type: Article
Times cited : (26)

References (38)
  • 1
    • 79960517189 scopus 로고    scopus 로고
    • Toxicological assessment of 2-methyltetrahydrofuran and cyclopentyl methyl ether in support of their use in pharmaceutical chemical process development
    • Antonucci V., Coleman J., Ferry J.B., Johnson N., Mathe M., Scott J.P., Xu J. Toxicological assessment of 2-methyltetrahydrofuran and cyclopentyl methyl ether in support of their use in pharmaceutical chemical process development. Org. Process Res. Dev. 2011, 15(4):939-941.
    • (2011) Org. Process Res. Dev. , vol.15 , Issue.4 , pp. 939-941
    • Antonucci, V.1    Coleman, J.2    Ferry, J.B.3    Johnson, N.4    Mathe, M.5    Scott, J.P.6    Xu, J.7
  • 2
    • 33847697029 scopus 로고    scopus 로고
    • Solvent applications of 2-methyltetrahydrofuran in organometallic and biphasic reactions
    • Aycock D.F. Solvent applications of 2-methyltetrahydrofuran in organometallic and biphasic reactions. Org. Process Res. Dev. 2007, 11(1):156-159.
    • (2007) Org. Process Res. Dev. , vol.11 , Issue.1 , pp. 156-159
    • Aycock, D.F.1
  • 4
    • 0038218020 scopus 로고    scopus 로고
    • Lipase-catalyzed synthesis of xylitol monoesters: solvent engineering approach
    • Castillo E., Pezzotti F., Navarro A., Lopez-Munguia A. Lipase-catalyzed synthesis of xylitol monoesters: solvent engineering approach. J. Biotechnol. 2003, 102(3):251-259.
    • (2003) J. Biotechnol. , vol.102 , Issue.3 , pp. 251-259
    • Castillo, E.1    Pezzotti, F.2    Navarro, A.3    Lopez-Munguia, A.4
  • 5
    • 30344486584 scopus 로고    scopus 로고
    • Antiviral prodrugs - the development of successful prodrug strategies for antiviral chemotherapy
    • De Clercq E., Field H.J. Antiviral prodrugs - the development of successful prodrug strategies for antiviral chemotherapy. Br. J. Pharmacol. 2006, 147(1):1-11.
    • (2006) Br. J. Pharmacol. , vol.147 , Issue.1 , pp. 1-11
    • De Clercq, E.1    Field, H.J.2
  • 6
    • 0035878796 scopus 로고    scopus 로고
    • 8-Chloro-cAMP and 8-chloro-adenosine act by the same mechanism in multiple myeloma cells
    • Gandhi V., Ayres M., Halgren R.G., Krett N.L., Newman R.A., Rosen S.T. 8-Chloro-cAMP and 8-chloro-adenosine act by the same mechanism in multiple myeloma cells. Cancer Res. 2001, 61(14):5474-5479.
    • (2001) Cancer Res. , vol.61 , Issue.14 , pp. 5474-5479
    • Gandhi, V.1    Ayres, M.2    Halgren, R.G.3    Krett, N.L.4    Newman, R.A.5    Rosen, S.T.6
  • 7
    • 80053201257 scopus 로고    scopus 로고
    • Highly regioselective synthesis of undecylenic acid esters of purine nucleosides catalyzed by Candida antarctica lipase B
    • Gao W.L., Li N., Zong M.H. Highly regioselective synthesis of undecylenic acid esters of purine nucleosides catalyzed by Candida antarctica lipase B. Biotechnol. Lett. 2011, 33(11):2233-2240.
    • (2011) Biotechnol. Lett. , vol.33 , Issue.11 , pp. 2233-2240
    • Gao, W.L.1    Li, N.2    Zong, M.H.3
  • 8
    • 77955035656 scopus 로고    scopus 로고
    • Selective and flexible transformation of biomass-derived platform chemicals by a multifunctional catalytic system
    • Geilen F.M.A., Engendahl B., Harwardt A., Marquardt W., Klankermayer J., Leitner W. Selective and flexible transformation of biomass-derived platform chemicals by a multifunctional catalytic system. Angew. Chem. Int. Ed. 2010, 49(32):5510-5514.
    • (2010) Angew. Chem. Int. Ed. , vol.49 , Issue.32 , pp. 5510-5514
    • Geilen, F.M.A.1    Engendahl, B.2    Harwardt, A.3    Marquardt, W.4    Klankermayer, J.5    Leitner, W.6
  • 9
    • 80052371428 scopus 로고    scopus 로고
    • Thermo-kinetics of lipase-catalyzed synthesis of 6-O-glucosyldecanoate
    • Gumel A.M., Annuar M.S.M., Heidelberg T., Chisti Y. Thermo-kinetics of lipase-catalyzed synthesis of 6-O-glucosyldecanoate. Bioresour. Technol. 2011, 102(19):8727-8732.
    • (2011) Bioresour. Technol. , vol.102 , Issue.19 , pp. 8727-8732
    • Gumel, A.M.1    Annuar, M.S.M.2    Heidelberg, T.3    Chisti, Y.4
  • 10
    • 79959625069 scopus 로고    scopus 로고
    • Optimised dynamic kinetic resolution of benzoin by a chemoenzymatic approach in 2-MeTHF
    • Hoyos P., Quezada M.A., Sinisterra J.V., Alcantara A.R. Optimised dynamic kinetic resolution of benzoin by a chemoenzymatic approach in 2-MeTHF. J. Mol. Catal. B: Enzym. 2011, 72(1-2):20-24.
    • (2011) J. Mol. Catal. B: Enzym. , vol.72 , Issue.1-2 , pp. 20-24
    • Hoyos, P.1    Quezada, M.A.2    Sinisterra, J.V.3    Alcantara, A.R.4
  • 11
    • 0031104802 scopus 로고    scopus 로고
    • Why are enzymes less active in organic solvents than in water?
    • Klibanov A.M. Why are enzymes less active in organic solvents than in water?. Trends Biotechnol. 1997, 15(3):97-101.
    • (1997) Trends Biotechnol. , vol.15 , Issue.3 , pp. 97-101
    • Klibanov, A.M.1
  • 12
    • 0026764144 scopus 로고
    • Growth inhibition of human glioma cells induced by 8-chloroadenosine, an active metabolite of 8-chloro cyclic adenosine 3': 5'-monophosphate
    • Langeveld C.H., Jongenelen C.A.M., Heimans J.J., Stoof J.C. Growth inhibition of human glioma cells induced by 8-chloroadenosine, an active metabolite of 8-chloro cyclic adenosine 3': 5'-monophosphate. Cancer Res. 1992, 52(14):3994-3999.
    • (1992) Cancer Res. , vol.52 , Issue.14 , pp. 3994-3999
    • Langeveld, C.H.1    Jongenelen, C.A.M.2    Heimans, J.J.3    Stoof, J.C.4
  • 13
    • 23644447557 scopus 로고    scopus 로고
    • An inverse substrate orientation for the regioselective acylation of 3',5'-diaminonucleosides catalyzed by Candida antarctica lipase B?
    • Lavandera I., Fernandez S., Magdalena J., Ferrero M., Kazlauskas R.J., Gotor V. An inverse substrate orientation for the regioselective acylation of 3',5'-diaminonucleosides catalyzed by Candida antarctica lipase B?. ChemBioChem 2005, 6(8):1381-1390.
    • (2005) ChemBioChem , vol.6 , Issue.8 , pp. 1381-1390
    • Lavandera, I.1    Fernandez, S.2    Magdalena, J.3    Ferrero, M.4    Kazlauskas, R.J.5    Gotor, V.6
  • 14
    • 42949174825 scopus 로고    scopus 로고
    • Prodrugs of nucleoside analogues for improved oral absorption and tissue targeting
    • Li F.J., Maag H., Alfredson T. Prodrugs of nucleoside analogues for improved oral absorption and tissue targeting. J. Pharm. Sci. 2008, 97(3):1109-1134.
    • (2008) J. Pharm. Sci. , vol.97 , Issue.3 , pp. 1109-1134
    • Li, F.J.1    Maag, H.2    Alfredson, T.3
  • 15
    • 77949570525 scopus 로고    scopus 로고
    • Biocatalytic transformation of nucleoside derivatives
    • Li N., Smith T.J., Zong M.H. Biocatalytic transformation of nucleoside derivatives. Biotechnol. Adv. 2010, 28(3):348-366.
    • (2010) Biotechnol. Adv. , vol.28 , Issue.3 , pp. 348-366
    • Li, N.1    Smith, T.J.2    Zong, M.H.3
  • 16
    • 77957852691 scopus 로고    scopus 로고
    • Lipases from the genus Penicillium: production, purification, characterization and applications
    • Li N., Zong M.H. Lipases from the genus Penicillium: production, purification, characterization and applications. J. Mol. Catal. B: Enzym. 2010, 66:43-54.
    • (2010) J. Mol. Catal. B: Enzym. , vol.66 , pp. 43-54
    • Li, N.1    Zong, M.H.2
  • 17
    • 34249296294 scopus 로고    scopus 로고
    • Regioselective synthesis of 3'-O-caproyl-floxuridine catalyzed by Pseudomonas cepacia lipase
    • Li N., Zong M.H., Liu X.M., Ma D. Regioselective synthesis of 3'-O-caproyl-floxuridine catalyzed by Pseudomonas cepacia lipase. J. Mol. Catal. B: Enzym. 2007, 47(1-2):6-12.
    • (2007) J. Mol. Catal. B: Enzym. , vol.47 , Issue.1-2 , pp. 6-12
    • Li, N.1    Zong, M.H.2    Liu, X.M.3    Ma, D.4
  • 18
    • 57349091377 scopus 로고    scopus 로고
    • Regioselective acylation of nucleosides catalyzed by Candida antarctica lipase B: Enzyme substrate recognition
    • Li N., Zong M.H., Ma D. Regioselective acylation of nucleosides catalyzed by Candida antarctica lipase B: Enzyme substrate recognition. Eur. J. Org. Chem. 2008, 32:5375-5378.
    • (2008) Eur. J. Org. Chem. , vol.32 , pp. 5375-5378
    • Li, N.1    Zong, M.H.2    Ma, D.3
  • 19
    • 64749107212 scopus 로고    scopus 로고
    • Highly efficient transformation of waste oil to biodiesel by immobilized lipase from Penicillium expansum
    • Li N.W., Zong M.H., Wu H. Highly efficient transformation of waste oil to biodiesel by immobilized lipase from Penicillium expansum. Process Biochem. 2009, 44(6):685-688.
    • (2009) Process Biochem. , vol.44 , Issue.6 , pp. 685-688
    • Li, N.W.1    Zong, M.H.2    Wu, H.3
  • 20
    • 40549089254 scopus 로고    scopus 로고
    • Chemoenzymatic synthesis, characterization, and controlled release of functional polymeric prodrugs with acyclovir as pendant
    • Li X., Wu Q., Zhang F., Lin X.F. Chemoenzymatic synthesis, characterization, and controlled release of functional polymeric prodrugs with acyclovir as pendant. J. Appl. Polym. Sci. 2008, 108(1):431-437.
    • (2008) J. Appl. Polym. Sci. , vol.108 , Issue.1 , pp. 431-437
    • Li, X.1    Wu, Q.2    Zhang, F.3    Lin, X.F.4
  • 21
    • 77149160599 scopus 로고    scopus 로고
    • Development of a biocatalytic process as an alternative to the (-)-DIP-Cl-mediated asymmetric reduction of a key intermediate of montelukast
    • Liang J., Lalonde J., Borup B., Mitchell V., Mundorff E., Trinh N., Kochrekar D.A., Nair Cherat R., Pai G.G. Development of a biocatalytic process as an alternative to the (-)-DIP-Cl-mediated asymmetric reduction of a key intermediate of montelukast. Org. Process Res. Dev. 2010, 14(1):193-198.
    • (2010) Org. Process Res. Dev. , vol.14 , Issue.1 , pp. 193-198
    • Liang, J.1    Lalonde, J.2    Borup, B.3    Mitchell, V.4    Mundorff, E.5    Trinh, N.6    Kochrekar, D.A.7    Nair Cherat, R.8    Pai, G.G.9
  • 22
    • 0028352433 scopus 로고
    • Effect of solvent on lipase-catalyzed transesterification in organic media
    • Nakamura K., Kinoshita M., Ohno A. Effect of solvent on lipase-catalyzed transesterification in organic media. Tetrahedron 1994, 50(16):4681-4690.
    • (1994) Tetrahedron , vol.50 , Issue.16 , pp. 4681-4690
    • Nakamura, K.1    Kinoshita, M.2    Ohno, A.3
  • 23
    • 80051589495 scopus 로고    scopus 로고
    • Highly efficient chemoselective N-TBS protection of anilines under exceptional mild conditions in the eco-friendly solvent 2-methyltetrahydrofuran
    • Pace V., Alcantara A.R., Holzer W. Highly efficient chemoselective N-TBS protection of anilines under exceptional mild conditions in the eco-friendly solvent 2-methyltetrahydrofuran. Green Chem. 2011, 13(8):1986-1989.
    • (2011) Green Chem. , vol.13 , Issue.8 , pp. 1986-1989
    • Pace, V.1    Alcantara, A.R.2    Holzer, W.3
  • 24
    • 84863515693 scopus 로고    scopus 로고
    • 2-Methyl-tetrahydrofuran (2-MeTHF): A biomass-derived solvent with broad application in organic chemistry
    • DOI: 10.1002/cssc.201100780.
    • Pace, V., Hoyos, P., Castoldi, L., María, P.D.d., Alcántara, A.R. 2012. 2-Methyl-tetrahydrofuran (2-MeTHF): A biomass-derived solvent with broad application in organic chemistry. ChemSusChem, DOI: 10.1002/cssc.201100780.
    • (2012) ChemSusChem
    • Pace, V.1    Hoyos, P.2    Castoldi, L.3    María, P.D.D.4    Alcántara, A.R.5
  • 25
    • 0037272860 scopus 로고    scopus 로고
    • Enzymatic synthesis of hydrophilic undecylenic acid sugar esters and their biodegradability
    • Raku T., Kitagawa M., Shimakawa H., Tokiwa Y. Enzymatic synthesis of hydrophilic undecylenic acid sugar esters and their biodegradability. Biotechnol. Lett. 2003, 25(2):161-166.
    • (2003) Biotechnol. Lett. , vol.25 , Issue.2 , pp. 161-166
    • Raku, T.1    Kitagawa, M.2    Shimakawa, H.3    Tokiwa, Y.4
  • 26
    • 33750601477 scopus 로고    scopus 로고
    • Purine nucleoside analogs as immunosuppressive and antineoplastic agents: mechanism of action and clinical activity
    • Robak T., Lech-Maranda E., Korycka A., Robak E. Purine nucleoside analogs as immunosuppressive and antineoplastic agents: mechanism of action and clinical activity. Curr. Med. Chem. 2006, 13(26):3165-3189.
    • (2006) Curr. Med. Chem. , vol.13 , Issue.26 , pp. 3165-3189
    • Robak, T.1    Lech-Maranda, E.2    Korycka, A.3    Robak, E.4
  • 27
    • 54749112196 scopus 로고    scopus 로고
    • Enantioselective Cu-catalyzed 1,4-addition of grignard reagents to cyclohexenone using Taddol-derived phosphine-phosphite ligands and 2-methyl-THF as a solvent
    • Robert T., Velder J., Schmalz H.-G. Enantioselective Cu-catalyzed 1,4-addition of grignard reagents to cyclohexenone using Taddol-derived phosphine-phosphite ligands and 2-methyl-THF as a solvent. Angew. Chem. Int. Ed. 2008, 47(40):7718-7721.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , Issue.40 , pp. 7718-7721
    • Robert, T.1    Velder, J.2    Schmalz, H.-G.3
  • 28
    • 84857155198 scopus 로고    scopus 로고
    • Oxidation-hydroxymethylation-reduction: a one-pot three-step biocatalytic synthesis of optically active α-aryl vicinal diols
    • Shanmuganathan S., Natalia D., Greiner L., Dominguez de Maria P. Oxidation-hydroxymethylation-reduction: a one-pot three-step biocatalytic synthesis of optically active α-aryl vicinal diols. Green Chem. 2012, 14(1):94-97.
    • (2012) Green Chem. , vol.14 , Issue.1 , pp. 94-97
    • Shanmuganathan, S.1    Natalia, D.2    Greiner, L.3    Dominguez de Maria, P.4
  • 29
    • 78649834833 scopus 로고    scopus 로고
    • Enzyme-catalyzed C-C bond formation using 2-methyltetrahydrofuran (2-MTHF) as (co)solvent: efficient and bio-based alternative to DMSO and MTBE
    • Shanmuganathan S., Natalia D., van den Wittenboer A., Kohlmann C., Greiner L., Dominguez de Maria P. Enzyme-catalyzed C-C bond formation using 2-methyltetrahydrofuran (2-MTHF) as (co)solvent: efficient and bio-based alternative to DMSO and MTBE. Green Chem. 2010, 12(12):2240-2245.
    • (2010) Green Chem. , vol.12 , Issue.12 , pp. 2240-2245
    • Shanmuganathan, S.1    Natalia, D.2    van den Wittenboer, A.3    Kohlmann, C.4    Greiner, L.5    Dominguez de Maria, P.6
  • 30
    • 67649103762 scopus 로고    scopus 로고
    • Regioselective enzymatic acylation of pharmacologically interesting nucleosides in 2-methyltetrahydrofuran, a greener substitute for THF
    • Simeo Y., Sinisterra J.V., Alcantara A.R. Regioselective enzymatic acylation of pharmacologically interesting nucleosides in 2-methyltetrahydrofuran, a greener substitute for THF. Green Chem. 2009, 11(6):855-862.
    • (2009) Green Chem. , vol.11 , Issue.6 , pp. 855-862
    • Simeo, Y.1    Sinisterra, J.V.2    Alcantara, A.R.3
  • 31
    • 34247850945 scopus 로고    scopus 로고
    • Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on melanin synthesis
    • Tokiwa Y., Kitagawa M., Raku T., Yanagitani S., Yoshino K. Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on melanin synthesis. Bioorg. Med. Chem. Lett. 2007, 17(11):3105-3108.
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , Issue.11 , pp. 3105-3108
    • Tokiwa, Y.1    Kitagawa, M.2    Raku, T.3    Yanagitani, S.4    Yoshino, K.5
  • 32
    • 69849103593 scopus 로고    scopus 로고
    • Undecylenic acid: a valuable and physiologically active renewable building block from castor oil
    • van der Steen M., Stevens C.V. Undecylenic acid: a valuable and physiologically active renewable building block from castor oil. ChemSusChem 2009, 2(8):692-713.
    • (2009) ChemSusChem , vol.2 , Issue.8 , pp. 692-713
    • van der Steen, M.1    Stevens, C.V.2
  • 34
    • 0034666525 scopus 로고    scopus 로고
    • Determination of pharmacokinetics of 8-chloroadenosine and its two major metabolites in dogs by high-performance liquid chromatography
    • Wang X., Zhang W., Zou A., Lou Y. Determination of pharmacokinetics of 8-chloroadenosine and its two major metabolites in dogs by high-performance liquid chromatography. J. Chromatogr. B 2000, 746(2):319-323.
    • (2000) J. Chromatogr. B , vol.746 , Issue.2 , pp. 319-323
    • Wang, X.1    Zhang, W.2    Zou, A.3    Lou, Y.4
  • 35
    • 0033575391 scopus 로고    scopus 로고
    • 'Watching' lipase-catalyzed acylations using 1H NMR: competing hydrolysis of vinyl acetate in dry organic solvents
    • Weber H.K., Weber H., Kazlauskas R.J. 'Watching' lipase-catalyzed acylations using 1H NMR: competing hydrolysis of vinyl acetate in dry organic solvents. Tetrahedron: Asymmetry 1999, 10(14):2635-2638.
    • (1999) Tetrahedron: Asymmetry , vol.10 , Issue.14 , pp. 2635-2638
    • Weber, H.K.1    Weber, H.2    Kazlauskas, R.J.3
  • 36
    • 70249110360 scopus 로고    scopus 로고
    • A highly regioselective route to arbutin esters by immobilized lipase from Penicillium expansum
    • Yang R.L., Li N., Li R.F., Smith T.J., Zong M.H. A highly regioselective route to arbutin esters by immobilized lipase from Penicillium expansum. Bioresour. Technol. 2010, 101(1):1-5.
    • (2010) Bioresour. Technol. , vol.101 , Issue.1 , pp. 1-5
    • Yang, R.L.1    Li, N.2    Li, R.F.3    Smith, T.J.4    Zong, M.H.5
  • 37
    • 77956924031 scopus 로고    scopus 로고
    • Highly regioselective synthesis of novel aromatic esters of arbutin catalyzed by immobilized lipase from Penicillium expansum
    • Yang R.L., Li N., Ye M., Zong M.H. Highly regioselective synthesis of novel aromatic esters of arbutin catalyzed by immobilized lipase from Penicillium expansum. J. Mol. Catal. B: Enzym. 2010, 67(1-2):41-44.
    • (2010) J. Mol. Catal. B: Enzym. , vol.67 , Issue.1-2 , pp. 41-44
    • Yang, R.L.1    Li, N.2    Ye, M.3    Zong, M.H.4
  • 38
    • 32844464689 scopus 로고    scopus 로고
    • Towards understanding the reaction pathway in vapour phase hydrogenation of furfural to 2-methylfuran
    • Zheng H.Y., Zhu Y.L., Teng B.T., Bai Z.Q., Zhang C.H., Xiang H.W., Li Y.W. Towards understanding the reaction pathway in vapour phase hydrogenation of furfural to 2-methylfuran. J. Mol. Catal. A: Chem. 2006, 246(1-2):18-23.
    • (2006) J. Mol. Catal. A: Chem. , vol.246 , Issue.1-2 , pp. 18-23
    • Zheng, H.Y.1    Zhu, Y.L.2    Teng, B.T.3    Bai, Z.Q.4    Zhang, C.H.5    Xiang, H.W.6    Li, Y.W.7


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