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

Fumihiko Iwasaki, Keishi Suga, Yukihiro Okamoto, Hiroshi Umakoshi

Research output: Contribution to journalArticle

8 Citations (Scopus)

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 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.

Original languageEnglish
Pages (from-to)91-97
Number of pages7
JournalACS Omega
Volume2
Issue number1
DOIs
Publication statusPublished - 2017 Jan 31
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Fingerprint Dive into the research topics of 'Liposomes Can Achieve Enantioselective C-C Bond Formation of an α-Amino Acid Derivative in Aqueous Media'. Together they form a unique fingerprint.

  • Cite this