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题名: Substantially enhancing enzymatic regioselective acylation of 1-beta-D-arabinofuranosylcytosine with vinyl caprylate by using a co-solvent mixture of hexane and pyridine
作者: 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
发表日期: 2008-10-01
DOI: 10.1016/j.cej.2008.05.010
卷: 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
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.
关键词[WOS]: ORGANIC-SYNTHESIS ;  NUCLEIC-ACIDS ;  NUCLEOSIDE ;  ENZYMES ;  SUGARS
语种: 英语
WOS记录号: WOS:000260039900010
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/140771
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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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

Recommended Citation:
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.
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