Chiral discrimination between thalidomide enantiomers using a solid surface with two-dimensional chirality.
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.
Nakanishi
Takuya
T
Department of Applied Chemistry, School of Science and Engineering, Waseda University, Tokyo, Japan.
Yamakawa
Naoko
N
Asahi
Toru
T
Shibata
Norio
N
Ohtani
Bunsho
B
Osaka
Tetsuya
T
D002264:Carboxylic Acids / Q000737:chemistry; D006046:Gold / Q000737:chemistry; D013237:Stereoisomerism; D013792:Thalidomide / Q000031:analogs & derivatives / Q000737:chemistry* / Q000494:pharmacology
D002264:Carboxylic Acids; D013792:Thalidomide; D006046:Gold; C046170:naphthenic acid