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Substantially enhancing enzymatic regioselective acylation of 1-beta-D-arabinofuranosylcytosine with vinyl caprylate by using a co-solvent mixture of hexane and pyridine
Zong, Min-Hua1; Wu, Hong1,2; Tan, Zi-yang1
关键词1-beta-d-arabinofuranosylcytosine Novozym 435 Acylation Vinyl Caprylate
刊名CHEMICAL ENGINEERING JOURNAL
2008-10-01
DOI10.1016/j.cej.2008.05.010
144期:1页:75-78
收录类别SCI
文章类型Article
WOS标题词Science & Technology ; Technology
类目[WOS]Engineering, Environmental ; Engineering, Chemical
研究领域[WOS]Engineering
关键词[WOS]ORGANIC-SYNTHESIS ; NUCLEIC-ACIDS ; NUCLEOSIDE ; ENZYMES ; SUGARS
英文摘要Novozym 435-catalyzed regioselective acylation of 1-beta-D-arabinofuranosylcytosine (ara-C) with vinyl caprylate for the preparation of its 5'-O-acyl derivative has been performed in six co-solvent mixtures and three pure polar solvents for the first time. Novozym 435 displayed low activity towards 1-beta-D-arabinofuranosylcytosine in pure polar solvents, although those solvents can dissolve the nucleosides well. When a hexane-pyridine co-solvent system was adopted, both the initial rate and the substrate conversion were enhanced markedly.The most suitable co-solvent, initial water activity, reaction temperature and the molar ratio of vinyl caprylate to ara-C were hexane/pyridine (28/72, v/v), 0.03, 40 degrees C and 15, respectively. Under these conditions, the initial rate, the substrate conversion and the regioselectivity were as high as 99.0 mmol h(-1), 98% and >99%, respectively. The product of the Novozym 435-catalyzed reaction was characterized by (13)C NMR and confirmed to be 5'-O-octanoyl 1-beta-D-arabinofuranosylcytosine. (C) 2008 Elsevier B.V. All rights reserved.
语种英语
WOS记录号WOS:000260039900010
引用统计
被引频次:3[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://cas-ir.dicp.ac.cn/handle/321008/140771
专题中国科学院大连化学物理研究所
作者单位1.S China Univ Technol, Lab Appl Biocatalysis, Guangzhou 510640, Peoples R China
2.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
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Zong, Min-Hua,Wu, Hong,Tan, Zi-yang. Substantially enhancing enzymatic regioselective acylation of 1-beta-D-arabinofuranosylcytosine with vinyl caprylate by using a co-solvent mixture of hexane and pyridine[J]. CHEMICAL ENGINEERING JOURNAL,2008,144(1):75-78.
APA Zong, Min-Hua,Wu, Hong,&Tan, Zi-yang.(2008).Substantially enhancing enzymatic regioselective acylation of 1-beta-D-arabinofuranosylcytosine with vinyl caprylate by using a co-solvent mixture of hexane and pyridine.CHEMICAL ENGINEERING JOURNAL,144(1),75-78.
MLA Zong, Min-Hua,et al."Substantially enhancing enzymatic regioselective acylation of 1-beta-D-arabinofuranosylcytosine with vinyl caprylate by using a co-solvent mixture of hexane and pyridine".CHEMICAL ENGINEERING JOURNAL 144.1(2008):75-78.
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