Synthesis and Properties of Alkyl Phosphorylcholine Amphiphiles with a Linear and an Asymmetrically Branched Alkyl Chain

Eui-Chul Kang; Shingo Kataoka; Kenji Kato

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Synthesis and Properties of Alkyl Phosphorylcholine Amphiphiles with a Linear and an Asymmetrically Branched Alkyl Chain

机译：具有直链和不对称支链烷基链的烷基磷酸胆碱两亲物的合成及性质

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Alkyl phosphorylcholine amphiphiles bearing one linear chain and one asymmetrically branched alkyl chain were successfully synthesized using 2-chloro-2-oxo-l,3,2-dioxaphospholane in tetrahydrofuran or ethyl acetate.~1H and 3IPNMR studies revealed that the linear alkyl phosphorylcholines(C_n-PC)provide aqueous micelles in D_2O and reverse micelles in CDCl_3,while the branched alkyl phosphorylcholines(ISOFOL_n-PC)give vesicles in D_2O.The critical micelle concentrations(CMCs)of C_n-PC were measured by fluorescence dye solubilization methods:the CMCs of C12-PC,C_(14)-PC,C16-PC,and C_(18)-PC were 1.6,0.38,0.16,and 0.11 mM,respectively,in water at 25 deg C.The critical association concentrations(CACs)of ISOFOL_(16)-PC,ISOFOL_(20)-PC,and ISOFOL_(24)-PC were 0.068,0.005,and 0.077 mM,respectively,in water at 25 deg C.The vesicle size of ISOFOL_n-PC in aqueous solution was measured by the dynamic light scattering method.The mean diameter of ISOFOL_n-PC vesicles was approximately 30 nm and the size distribution was relatively monodisperse.The ISOFOL)_nPC vesicles formed were colloidally stable in water over the period of several weeks.

机译：用2-氯-2-氧代-1,3,2-二氧杂膦环烷在四氢呋喃或乙酸乙酯中成功合成了带有一条线性链和一条不对称支链烷基链的烷基磷酸胆碱两亲物。〜1H和3IPNMR研究表明，线性烷基磷酰胆碱（ C_n-PC）在D_2O中提供水性胶束，在CDCl_3中提供反胶束，而支链烷基磷酸胆碱（ISOFOL_n-PC）则在D_2O中提供囊泡。在25°C的水中，C12-PC，C_（14）-PC，C16-PC和C_（18）-PC的CMC分别为1.6、0.38、0.16和0.11 mM。在25°C的水中，ISOFOL_（16）-PC，ISOFOL_（20）-PC和ISOFOL_（24）-PC的）分别为0.068、0.005和0.077 mM。用动态光散射法测定溶液的浓度。ISOFOL_n-PC囊泡的平均直径约为30 nm，s的分布是相对分散的。形成的ISOFOL_nPC囊泡在水中几周内是胶体稳定的。

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《Bulletin of the Chemical Society of Japan》 |2005年第8期|共7页
作者
Eui-Chul Kang; Shingo Kataoka; Kenji Kato;
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Synthesis and Properties of Alkyl Phosphorylcholine Amphiphiles with a Linear and an Asymmetrically Branched Alkyl Chain

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