title: Chiral discrimination between thalidomide enantiomers using a solid surface with two-dimensional chirality.
abstract: Chiral discrimination between thalidomide enantiomers was achieved using the self-assembled monolayer (SAM) of an atropisomeric compound, 1,1'-binaphthalene-2,2'-dithiol (BNSH), which takes a two-dimensional chiral arrangement on gold(111) surface. Interestingly, an "all-or-none" type enantioselectivity appears; one enantiomeric form of BNSH SAM allows the adsorption of only one enantiomer of thalidomide. In addition, the response of a racemic SAM of BNSH was revealed to be one-half of that caused by pure enantiomeric SAM.
authors.affiliation: Department of Applied Chemistry, School of Science and Engineering, Waseda University, Tokyo, Japan.
authors.forename: Takuya
authors.initials: T
authors.lastname: Nakanishi
authors.forename: Naoko
authors.initials: N
authors.lastname: Yamakawa
authors.forename: Toru
authors.initials: T
authors.lastname: Asahi
authors.forename: Norio
authors.initials: N
authors.lastname: Shibata
authors.forename: Bunsho
authors.initials: B
authors.lastname: Ohtani
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Osaka
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry; D006046:Gold / Q000737:chemistry; D013237:Stereoisomerism; D013792:Thalidomide / Q000031:analogs & derivatives / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D002264:Carboxylic Acids; D013792:Thalidomide; D006046:Gold; C046170:naphthenic acid