混合溶剂体系中牛肝 β-半乳糖苷酶催化 5-氟-2'-脱氧尿苷区域选择性半乳糖基化反应

doi:10.3724/SP.J.1088.2011.01150

催化学报 ›› 2011, Vol. 32 ›› Issue (6): 1063-1068.DOI: 10.3724/SP.J.1088.2011.01150

混合溶剂体系中牛肝 β-半乳糖苷酶催化 5-氟-2'-脱氧尿苷区域选择性半乳糖基化反应

叶敏 1, 刘秋萍 1, 李宁 2,3,a, 宗敏华 2,b

1华南理工大学生物科学与工程学院, 广东广州 510006; 2华南理工大学轻工与食品学院制浆造纸工程国家重点实验室, 广东广州 510640; 3中国科学院大连化学物理研究所催化基础国家重点实验室, 辽宁大连 116023

收稿日期:2010-11-19 修回日期:2011-03-11 出版日期:2011-06-21 发布日期:2014-10-31

Regioselective Galactosylation of Floxuridine Catalyzed by β-Galactosidase from Bovine Liver in Co-solvent Systems

YE Min1, LIU Qiuping1, LI Ning2,3,a, ZONG Minhua2,b

1School of Biosciences and Bioengineering, South China University of Technology, Guangzhou 510006, Guangdong, China; 2State Key Laboratory of Pulp and Paper Engineering, College of Light Industry and Food Sciences, South China University of Technology, Guangzhou 510640, Guangdong, China; 3State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China

Received:2010-11-19 Revised:2011-03-11 Online:2011-06-21 Published:2014-10-31

摘要/Abstract

摘要： 研究了混合溶剂体系中有机溶剂种类和含量对牛肝 β-半乳糖苷酶催化 5-氟-2'-脱氧尿苷区域选择性半乳糖基化反应的影响. 结果表明, 在含 10% (体积分数) 有机溶剂体系中, 该酶稳定性差, 失活严重. 减少有机溶剂含量可显著减轻其对该酶的毒害作用. 然而, 有机溶剂的添加对酶促糖基化反应的区域选择性的影响很小 (均保持在 99% 以上). 牛肝 β-半乳糖苷酶在混合溶剂体系中的催化性能与有机溶剂的介电常数有良好的相关性, 其中在含二甲亚砜 (DMSO) 体系中该酶催化活性最高. 当体系中 DMSO 含量 ≤ 5% 时, 目标产物收率达 71%.

关键词: β-半乳糖苷酶, 糖基化反应, 区域选择性, 5-氟-2'-脱氧尿苷, 有机溶剂

Abstract: The influence of organic solvents and their contents on the regioselective galactosylation of floxuridine catalyzed by β-galactosidase from bovine liver was investigated in co-solvent systems. It was revealed that the enzyme was unstable and inactivated substantially in organic solvent (10%, v/v)-containing systems, and the detrimental impacts of organic solvents on the enzyme could be relieved remarkably by decreasing their contents. Nevertheless, the addition of organic solvents exerted no influence on the regioselectivity of the enzymatic glycosylation, which retained >99%. The catalytic performance of β-galactosidase from bovine liver correlated well with the dielectric constants of organic solvents in co-solvent systems, among which the enzyme displayed the highest activity in dimethyl sulfoxide (DMSO)-containing system. The yield of desired product reached 71% when the DMSO content was less than 5% (v/v) in the medium.

Key words: β-galactosidase, glycosylation, regioselectivity, floxuridine, organic solvent

叶敏, 刘秋萍, 李宁, 宗敏华. 混合溶剂体系中牛肝 β-半乳糖苷酶催化 5-氟-2'-脱氧尿苷区域选择性半乳糖基化反应[J]. 催化学报, 2011, 32(6): 1063-1068.

YE Min, LIU Qiu-Ping, LI Ning, ZONG Min-Hua. Regioselective Galactosylation of Floxuridine Catalyzed by β-Galactosidase from Bovine Liver in Co-solvent Systems[J]. Chinese Journal of Catalysis, 2011, 32(6): 1063-1068.

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参考文献

1Chabner B A, Ryan D P, Paz-Ares L, Garcia-Carbonero R, Calabresi P. In: Hardman J G, Limbird L E eds. Goodman & Gilman’s The Pharmacological Basis of Therapeutics. 10th Ed. New York: McGraw-Hill, 2001. 1389
2Watanabe K A, Matsuda A, Halat M J, Hollenberg D H, Nisselbaum J S, Fox J J. J Med Chem, 1981, 24: 893
3Abraham R, Aman N, von Borstel R, Darsley M, Kamireddy B, Kenten J, Morris G, Titmas R. Cell Biochem Biophys, 1994, 24: 127
4Efimtseva E V, Mikhailov S N. Russ Chem Rev, 2004, 73: 401
5Efimtseva E V, Kulikova I V, Mikhailov S N. Mol Biol, 2009, 43: 301
6De Clercq E, Field H J. Br J Pharmacol, 2006, 147: 1
7Kim S H, Yoo S-M, Park I S, Kim Y H. J Nat Prod, 2000, 63: 1188
8Efimtseva E V, Kulikova I V, Mikhailov S N. Curr Org Chem, 2007, 11: 337
9Liu Z J, Zhou M, Min J M, Zhang L H. Tetrahedron: Asymmetry, 1999, 10: 2119
10Binder W H, Kahlig H, Schmid W. Tetrahedron: Asymmetry, 1995, 6: 1703
11Andreotti G, Trincone A, Giordano A. J Mol Catal B, 2007, 47: 28
12Zeng Q M, Li N, Zong M H. Biotechnol Lett, 2010, 32: 1251
13Li N, Smith T J, Zong M H. Biotechnol Adv, 2010, 28: 348
14Shin H J, Yang J W. Biotechnol Lett, 1994, 16: 1157
15Yoon J H, Rhee J S. Carbohydr Res, 2000, 327: 377
16Hansson T, Adlercreutz P. Biotechnol Bioeng, 2001, 75: 656
17Bridiau N, Issaoui N, Maugard T. Biotechnol Prog, 2010, 26: 1278
18Kaftzik N, Wasserscheid P, Kragl U. Org Process Res Dev, 2002, 6: 553
19Affleck R, Haynes C A, Clark D S. Proc Natl Acad Sci U S A, 1992, 89: 5167
20Li N, Zong M H, Liu X M, Ma D. J Mol Catal B, 2007, 47: 6
21Dean J A. Lange’s Handbook of Chemistry. 15th Ed. New York: McGraw-Hill, 1998. 5.105
22Laane C, Boeren S, Vos K, Veeger C. Biotechnol Bioeng, 1987, 30: 81
23Prodanovic R, Milosavic N, Jovanovic S, Prodanovic O, Velickovic T C, Vujcic Z, Jankov R M. Biocatal Biotransform, 2006, 24: 195
24Majumder A B, Singh B, Gupta M N. Bioorg Med Chem Lett, 2008, 18: 124
25Knapp S, Dong Y, Rupitz K, Withers S G. Bioorg Med Chem Lett, 1995, 5: 763
26Lang M, Kamrat T, Nidetzky B. Biotechnol Bioeng, 2006, 95: 1093

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混合溶剂体系中牛肝 β-半乳糖苷酶催化 5-氟-2'-脱氧尿苷区域选择性半乳糖基化反应

Regioselective Galactosylation of Floxuridine Catalyzed by β-Galactosidase from Bovine Liver in Co-solvent Systems

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