对硝基苯基α-L-阿拉伯呋喃糖苷的乙酸酯——通过脂肪酶作用进行区域选择性制备
The acetates of p-nitrophenyl alpha-L-arabinofuranoside--regioselective preparation by action of lipases.
作者信息
Mastihubová Mária, Szemesová Jana, Biely Peter
机构信息
Institute of Chemistry, Slovak Academy of Sciences, SK-845 38 Bratislava, Slovakia.
出版信息
Bioorg Med Chem. 2006 Mar 15;14(6):1805-10. doi: 10.1016/j.bmc.2005.10.023. Epub 2005 Nov 8.
All possible di-O-acetates and mono-O-acetates of p-nitrophenyl alpha-L-arabinofuranoside were prepared by chemoenzymatic way using lipases. The 2,3-di-O-acetate was obtained in 90% yield by deacetylation of the primary acetyl group of per-O-acetylated p-nitrophenyl alpha-L-arabinofuranoside by Candida cylindracea lipase (CCL) or Candida rugosa lipase (LAY). The 2,5- and 3,5-di-O-acetates were obtained by acetylation of p-nitrophenyl alpha-L-arabinofuranoside by Pseudomonas cepacia lipase (LPS-30) in organic solvents. The 5-O-acetate was regioselectively synthesised in 95% yield by acetylation of p-nitrophenyl alpha-L-arabinofuranoside catalysed by porcine pancreas lipase. Finally, the 2- and 3-O-acetates of p-nitrophenyl alpha-L-arabinofuranoside were obtained in two steps. The enzymatic di-O-acetylation of p-nitrophenyl alpha-L-arabinofuranoside by LPS-30 was followed by enzymatic hydrolysis of the primary acetyl group by CCL or LAY.
通过化学酶法利用脂肪酶制备了对硝基苯基α-L-阿拉伯呋喃糖苷的所有可能的二-O-乙酸酯和单-O-乙酸酯。通过柱状假丝酵母脂肪酶（CCL）或皱褶假丝酵母脂肪酶（LAY）对全-O-乙酰化对硝基苯基α-L-阿拉伯呋喃糖苷的伯乙酰基进行脱乙酰化反应，以90%的产率获得了2,3-二-O-乙酸酯。通过洋葱假单胞菌脂肪酶（LPS-30）在有机溶剂中对对硝基苯基α-L-阿拉伯呋喃糖苷进行乙酰化反应，获得了2,5-和3,5-二-O-乙酸酯。通过猪胰脂肪酶催化对对硝基苯基α-L-阿拉伯呋喃糖苷进行乙酰化反应，以95%的产率区域选择性地合成了5-O-乙酸酯。最后，通过两步法获得了对硝基苯基α-L-阿拉伯呋喃糖苷的2-和3-O-乙酸酯。先用LPS-30对对硝基苯基α-L-阿拉伯呋喃糖苷进行酶促二-O-乙酰化反应，然后用CCL或LAY对伯乙酰基进行酶促水解反应。
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