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首页> 外文期刊>ACS Omega >Liposomes Can Achieve Enantioselective C–C Bond Formation of an α-Amino Acid Derivative in Aqueous Media
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Liposomes Can Achieve Enantioselective C–C Bond Formation of an α-Amino Acid Derivative in Aqueous Media

机译：脂质体可以在水性介质中达到α-氨基酸衍生物的映选择性C-C键形成

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We first report that a highly enantioselective C–C bond formation reaction was achieved with liposomes in aqueous media. Alkylation of N -(diphenylmethylene)glycine tert -butyl ester (DMGBE) with benzyl bromide was conducted in the presence of cetyltrimethylammonium bromide micelles, resulting in a high conversion of DMGBE but little enantiomeric excess (e.e. ) of the product. The same reaction was then carried out in 1,2-dioleoyl-sn -glycero-3-phosphocholine liposome suspensions, where the e.e. values were high (at least 90 % (S)), indicating that the liposome membranes can behave as the promoter of the enantioselective reaction. Changing the type of lipid to 1,2-dipalmitoyl-sn -glycero-3-phosphocholine to form a more ordered bilayer membrane lowered the reaction conversion but still maintained high e.e. % , that is, >90 (S), regardless of lipid chirality. It is indicated that multiple interactions between the DMGBE intermediate and lipid molecules promoted the migration of the intermediate into the interior of the membrane, whose bottom side (Si face) could be free for alkylation. These results suggest that liposomes can promote and regulate the alkylation of amino acid derivatives.
机译：首先报告，在含水介质中使用脂质体实现高度映选择性的C-C键形成反应。在甲丁基三甲基溴化甲锭胶束存在下，在存在苄基溴化苄基溴乙酰丁二醇酯（DMGBE）与苄基溴的烷基化，导致DMGBE的高转化率，但小对映体过量（ ee ）产品。然后在1,2-Dioleyoyl- Sn-甘油-3-普啉甲胺脂质体悬浮液中进行相同的反应，其中例如。值高（至少90％），表明脂质体膜可以表现为对映选择性反应的启动子。改变脂质的类型至1,2-Dipalmitoyl- Sn-甘油-3-磷光啉，以形成更有序的双层膜降低了反应转化，但仍保持高 90（s），无论脂质手性如何。结果表明，DMGBE中间体和脂质分子之间的多种相互作用促进中间体进入膜的内部的迁移，其底侧（氏Si面）可以是自由的烷基化。这些结果表明脂质体可以促进和调节氨基酸衍生物的烷基化。

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