Paczkowski Cezary, Musial Arkadiusz, Wlodkowski Leszek, Kalinowska Malgorzata, Wojciechowski Zdzislaw A
Faculty of Biology, Department of Biochemistry, Warsaw University, Miecznikowa 1, 02-096, Warsaw, Poland.
Biotechnol Lett. 2007 Sep;29(9):1403-8. doi: 10.1007/s10529-007-9400-z. Epub 2007 Jun 5.
The regioselective acylation of cholesteryl beta-D-glucoside, at the C-6 of the glucose moiety, was achieved using microbial lipases in organic solvents. With palmitic acid as an acyl donor 81 or 63% conversions of cholesteryl glucoside to its 6'-O-palmitoyl derivative were obtained using Candida antarctica or Rhizomucor miehei enzymes, respectively. High yields (64-92%) were also obtained with fatty acids 6:0-22:0 and 16:1 (n-7). The synthesis of cholesteryl (6'-O-palmitoyl)glucoside was also achieved via transesterification, using mono-, di- and tri-palmitoylglycerols or methyl and ethyl palmitate as acyl sources. With R. miehei lipase transesterification between methyl palmitate (80 mM) and cholesteryl glucoside (1 mM) proceeded after 24 h with a nearly quantitative yield (97%).
在有机溶剂中使用微生物脂肪酶实现了胆固醇β-D-葡萄糖苷在葡萄糖部分C-6位的区域选择性酰化。以棕榈酸作为酰基供体，分别使用南极假丝酵母或米黑根毛霉脂肪酶时，胆固醇葡萄糖苷转化为其6'-O-棕榈酰衍生物的转化率分别为81%或63%。使用碳链长度为6:0 - 22:0和16:1（n-7）的脂肪酸也能获得高产率（64 - 92%）。还通过酯交换反应实现了胆固醇（6'-O-棕榈酰）葡萄糖苷的合成，使用单棕榈酰甘油、二棕榈酰甘油、三棕榈酰甘油或棕榈酸甲酯和乙酯作为酰基来源。使用米黑根毛霉脂肪酶时，棕榈酸甲酯（80 mM）与胆固醇葡萄糖苷（1 mM）之间的酯交换反应在24小时后进行，产率接近定量（97%）。
