Apte S S, Weber N, Mangold H K
Bundesanstalt für Fettforschung, H.P. Kaufmann Institut, Münster, FRG.
FEBS Lett. 1990 Jun 4;265(1-2):104-6. doi: 10.1016/0014-5793(90)80894-o.
Biotransformation of rac-1(3)-O-hexadecylglycerol by photomixotrophic rape (Brassica napus) cells in suspension culture leads to 1-O-hexadecyl-2-acyl-sn-glycero-3-phosphocholines and small proportions of other ether lipids, e.g. 1-O-hexadecyl-2-acyl-sn-glycero-3-phosphoethanolamines. Reaction of the hexadecylacyl-glycerophosphocholines with ethanolamine in the presence of phospholipase D from Streptomyces chromofuscus yields additional hexadecylacylglycerophosphoethanolamines. Partial hydrolysis of the combined hexadecylacylglycerophosphoethanolamines followed by reacylation of the resulting lyso compound with palmitic anhydride gives 1-O-hexadecyl-2-palmitoyl-sn-glycero-3-phospho-(N-palmitoyl) ethanolamine, a nontoxic ether glycerophospholipid with antitumor activity. The corresponding 1-O-tetradecyl,1-O-octadecyl, and 1-O-[(Z)-9'-octadecnyl] derivatives are prepared similarly.
悬浮培养的光养混合营养型油菜（甘蓝型油菜）细胞对消旋-1(3)-O-十六烷基甘油进行生物转化，生成1-O-十六烷基-2-酰基-sn-甘油-3-磷酸胆碱以及少量其他醚脂，例如1-O-十六烷基-2-酰基-sn-甘油-3-磷酸乙醇胺。在来自暗褐链霉菌的磷脂酶D存在的情况下，十六烷基酰基甘油磷酸胆碱与乙醇胺反应生成更多的十六烷基酰基甘油磷酸乙醇胺。对混合的十六烷基酰基甘油磷酸乙醇胺进行部分水解，然后将所得的溶血化合物与棕榈酸酐进行再酰化反应，得到1-O-十六烷基-2-棕榈酰基-sn-甘油-3-磷酸-(N-棕榈酰基)乙醇胺，这是一种具有抗肿瘤活性的无毒醚甘油磷脂。相应的1-O-十四烷基、1-O-十八烷基和1-O-[(Z)-9'-十八烯基]衍生物也以类似方式制备。
