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      Regioselective Enzymatic Procedure for Preparing 3'-O-stearoyl-6- azauridine by Using Burkholderia cepacia Lipase

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      https://www.riss.kr/link?id=A103816509

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      다국어 초록 (Multilingual Abstract)

      Previous studies on the lipase-mediated acylation of 6-azauridine with vinyl stearate in organic solvents revealed that while preparing a potential prodrug, 3'-Ostearoyl-6-azauridine, a lipase from Burkholderia cepacia showed high regioselectivity tow...

      Previous studies on the lipase-mediated acylation of 6-azauridine with vinyl stearate in organic solvents revealed that while preparing a potential prodrug, 3'-Ostearoyl-6-azauridine, a lipase from Burkholderia cepacia showed high regioselectivity toward the second hydroxyl group. The most suitable reaction solvent, molar ratio of vinyl stearate to 6-azauridine, and reaction temperature were anhydrous acetone, 15:1, and 45°C, respectively. Under these conditions, the initial reaction rate, 3'-regioselectivity,and maximum substrate conversion were as high as 10.4mM/h, 86.0, and 99.0%, respectively.

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      참고문헌 (Reference)

      1 Weber, H. K., "Watching lipase-catalyzed acylations using 1H NMR: Competing hydrolysis of vinyl acetate in dry organic solvents" 10 : 2635-2638, 1999

      2 Halling, P. J., "Thermodynamic predictions for biocatalysis in nonconventional media: theory, tests, and recommendations for experimental design and analysis" 16 : 178-206, 1994

      3 Pejanovi, V., "Synthesis and biological activity of some new 5'-O-acyl tiazofurin derivatives" 41 : 503-512, 2006

      4 Bello, A. M., "Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents. J. Med. Chem" 52 : 1648-1658, 2009

      5 Kumar, V., "Structural modifications of nucleosides in ionic liquids" 92 : 1260-1265, 2010

      6 Tsikaris, V., "Significance of bound residual water in the DMSO solution structure of stable peptide hydrates" 9 : 1353-1357, 1991

      7 Anthonsen, T., "Resolution of derivatives of 1, 2-propanediol with lipase B from Candida antarctica: Effect of substrate structure, medium, water activity and acyl donor on enantiomeric ratio" 93 : 199-207, 1998

      8 Zeng, H., "Resistance to purine and pyrimidine nucleoside and nucleobase analogs by the human MDR1 transfected murine leukemia cell line L1210/ VMDRC. 06" 68 : 911-921, 2004

      9 Almarsson, O., "Remarkable activation of enzymes in nonaqueous media by denaturing organic cosolvents" 49 : 87-92, 1996

      10 Li, N., "Regioselective acylation of nucleosides catalyzed by Candida Antarctica lipase B: Enzyme substrate recognition" 2008 : 5375-5378, 2008

      1 Weber, H. K., "Watching lipase-catalyzed acylations using 1H NMR: Competing hydrolysis of vinyl acetate in dry organic solvents" 10 : 2635-2638, 1999

      2 Halling, P. J., "Thermodynamic predictions for biocatalysis in nonconventional media: theory, tests, and recommendations for experimental design and analysis" 16 : 178-206, 1994

      3 Pejanovi, V., "Synthesis and biological activity of some new 5'-O-acyl tiazofurin derivatives" 41 : 503-512, 2006

      4 Bello, A. M., "Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents. J. Med. Chem" 52 : 1648-1658, 2009

      5 Kumar, V., "Structural modifications of nucleosides in ionic liquids" 92 : 1260-1265, 2010

      6 Tsikaris, V., "Significance of bound residual water in the DMSO solution structure of stable peptide hydrates" 9 : 1353-1357, 1991

      7 Anthonsen, T., "Resolution of derivatives of 1, 2-propanediol with lipase B from Candida antarctica: Effect of substrate structure, medium, water activity and acyl donor on enantiomeric ratio" 93 : 199-207, 1998

      8 Zeng, H., "Resistance to purine and pyrimidine nucleoside and nucleobase analogs by the human MDR1 transfected murine leukemia cell line L1210/ VMDRC. 06" 68 : 911-921, 2004

      9 Almarsson, O., "Remarkable activation of enzymes in nonaqueous media by denaturing organic cosolvents" 49 : 87-92, 1996

      10 Li, N., "Regioselective acylation of nucleosides catalyzed by Candida Antarctica lipase B: Enzyme substrate recognition" 2008 : 5375-5378, 2008

      11 Li, N., "Regioselective acylation of nucleosides and their analogs catalyzed by Pseudomonas cepacia lipase: Enzyme substrate recognition" 65 : 1063-1068, 2009

      12 Wang, Z. Y., "Recognition of acyl donors by lipase CAL-B in the acylation of 6-azauridine" 25 : 784-791, 2009

      13 Hamamura, E. K., "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) cytosine hydrochloride" 19 : 654-662, 1976

      14 Soares, C. M., "Protein structure and dynamics in nonaqueous solvents: INSIGHTS from molecular dynamics simulation studies" 84 : 1628-1641, 2003

      15 Zinni, M. A., "Preparation of potential 3-deazauridine and 6-azauridine prodrugs through an enzymatic alcoholysis" 47 : 86-90, 2007

      16 Díaz-Rodríguez, A., "Novel chemoenzymatic protocol for the synthesis of 3-O-dimethoxytrityl-2-deoxynucleoside derivatives as building blocks for oligonucleotide synthesis" 10 : 581-587, 2006

      17 Wang, H., "Novel and highly regioselective route for synthesis of 5-fluorouridine lipophilic ester derivatives by lipozyme TL IM" 129 : 689-695, 2007

      18 Chamouleau, F., "Influence of water activity and water content on sugar esters lipase-catalyzed synthesis in organic media" 11 : 949-954, 2001

      19 Klibanov, A. M., "Improving enzymes by using them in organic solvents" 409 : 241-246, 2001

      20 Lum, P. Y., "Human intestinal es nucleoside transporter: Molecular characterization and nucleoside inhibitory profiles" 45 : 273-278, 2000

      21 Li, X. F., "Highly regioselective enzymatic synthesis of 5'-O-stearate of 1-β-D-arabinofuranosylcytosine in binary organic solvent mixtures" 88 : 2010

      22 Plevová, J., "Elimination of 2',3',5'-tri-O-acetyl-6-azauridine in the rat and in man" 20 : 2079-2083, 1971

      23 Ferrero, M., "Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides, and C-nucleosides" 100 : 4319-4348, 2000

      24 Bell, G., "Biocatalyst behaviour in low-water systems" 13 : 468-473, 1995

      25 Wang, Z. Y., "A simple procedure for the synthesis of potential 6-azauridine prodrugs by Thermomyces lanuginosus lipase" 59 : 212-219, 2009

      26 Clercq, E. De, "40-year journey in the antiviral drug field" 51 : 1-24, 2011

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      학술지 이력

      학술지 이력
      연월일 이력구분 이력상세 등재구분
      2023 평가예정 해외DB학술지평가 신청대상 (해외등재 학술지 평가)
      2020-01-01 평가 등재학술지 유지 (해외등재 학술지 평가) KCI등재
      2011-01-01 평가 등재학술지 유지 (등재유지) KCI등재
      2009-01-01 평가 등재학술지 유지 (등재유지) KCI등재
      2007-01-01 평가 등재학술지 유지 (등재유지) KCI등재
      2004-01-01 평가 등재학술지 선정 (등재후보2차) KCI등재
      2003-01-01 평가 등재후보 1차 PASS (등재후보1차) KCI등재후보
      2001-07-01 평가 등재후보학술지 선정 (신규평가) KCI등재후보
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      학술지 인용정보
      기준연도 WOS-KCI 통합IF(2년) KCIF(2년) KCIF(3년)
      2016 1.14 0.13 0.75
      KCIF(4년) KCIF(5년) 중심성지수(3년) 즉시성지수
      0.57 0.46 0.239 0.02
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