Doerr I L, Tang J C, Rosenthal A F, Engel R, Tropp B E
Chem Phys Lipids. 1977 Jul;19(3):185-202. doi: 10.1016/0009-3084(77)90042-1.
The chemical synthesis of four phosphonate-containing phosphatidylserine analogs namely, L-serine (+/-)-[2,3-bis(hexadecyloxy) and 2,3-bis(Palmitoyloxy)-propyl] phosphonates, and L-serine (+/-)-[3,4-bis(hexadecyloxy and 3,4-bis(palmitoyloxy)-butyL]phosphonates is descirbed. (+/-)-2,3-Bis(hexadecyloxy) and 2,3-bis(palmitoyloxy)-prophylphosphonic acids and (+/-)-3,4-bis(hexadecyloxy)butylphosponic acid were prepared by reaction of tris(trimethylsily) phosphite on the corresponding haloalkane. Condensation of the above phosphonic acids or (+/-)-3,4-bis(palmitoyloxy)butylphosphonic acid with N-carboxy-L-serine dibenzyl ester in the presence of trichloroacetonitrile or triisopropylbenzenesulfonyl chloride yielded the protected serine intermediates, which on hydrogenolysis gave the desired L-serine analogs. By a similar route, 1,2-dihexadecyl-rac-glycero-3-phosphoric acid was converted to 1,2-dihexadecyl-rac-glycerophospho-L-serine (L-serine (+/-)-2,3-bis(hexadecyloxy)propyl hydrogen phosphate(ester).
本文描述了四种含膦酸酯的磷脂酰丝氨酸类似物的化学合成，即L-丝氨酸（±）-[2,3-双（十六烷氧基）和2,3-双（棕榈酰氧基）丙基]膦酸酯，以及L-丝氨酸（±）-[3,4-双（十六烷氧基）和3,4-双（棕榈酰氧基）丁基]膦酸酯。（±）-2,3-双（十六烷氧基）和2,3-双（棕榈酰氧基）丙基膦酸以及（±）-3,4-双（十六烷氧基）丁基膦酸是通过亚磷酸三（三甲基硅基）酯与相应的卤代烷反应制备的。上述膦酸或（±）-3,4-双（棕榈酰氧基）丁基膦酸与N-羧基-L-丝氨酸二苄酯在三氯乙腈或三异丙基苯磺酰氯存在下缩合，得到受保护的丝氨酸中间体，该中间体经氢解得到所需的L-丝氨酸类似物。通过类似的路线，1,2-二己基-外消旋甘油-3-磷酸被转化为1,2-二己基-外消旋甘油磷酰-L-丝氨酸（L-丝氨酸（±）-2,3-双（十六烷氧基）丙基磷酸氢酯）。
