期刊
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
卷 88, 期 1, 页码 57-63出版社
SPRINGER
DOI: 10.1007/s00253-010-2705-1
关键词
1-beta-D-arabinofuranosylcytosine; Vinyl stearate; Lipases; Binary organic solvents
资金
- National Natural Science Foundation of China [20906031]
- Science and Technology Project of Guangdong Province [8451064101000807]
- South China University of Technology [2009ZZ0020]
- Doctoral Program of Higher Education [200805611022, 200805611104]
In this paper, highly regioselective enzymatic acylations of 1-beta-D-arabinofuranosylcytosine (ara-C) with vinyl stearate (VS) in binary organic solvents were explored for the preparation of 5'-O-stearate of ara-C with potential antitumor activity. Twelve kinds of hydrolases were tested for the regioselective acylation reaction and the immobilized Candida antarctica lipase B (Novozym 435) showed the highest regioselectivity (>99.9%) towards the 5'-OH of ara-C. A comparative study showed that the lipase had much higher catalytic activity in the binary mixture of hexane and pyridine than in other tested co-solvent systems. To better understand lipase-mediated acylation conducted in the best binary organic solvent system, the effects of hydrophobic solvent content, molar ratio of VS to ara-C, initial water activity, and reaction temperature on the acylation reaction were studied. It was found that the most suitable hexane content, VS-ara-C molar ratio, initial water activity, and reaction temperature were shown to be 25% (v/v), 20:1, 0.07, and 50 degrees C, respectively. Under these reaction conditions, the initial reaction rate, the maximum substrate conversion, and regioselectivity were as high as 86.0 mmol.L(-1)h(-1), 96.6%, and >99.9%, respectively. The product of Novozym 435-catalyzed acylation was characterized by Carbon-13(C-13) NMR and confirmed to be 5'-O-stearate of ara-C.
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