Liposomes Can Achieve Enantioselective C-C Bond Formation of an α-Amino Acid Derivative in Aqueous Media.

ABSTRACT: 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 reac

SUBMITTER: Iwasaki F 

PROVIDER: S-EPMC6640982 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature