Chiral discrimination between thalidomide enantiomers using a solid surface with two-dimensional chirality

Chirality
Takuya NakanishiTetsuya Osaka

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.

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Citations

Jan 1, 2010·Sensors·Katsuhiko ArigaJonathan P Hill
Jan 13, 2006·Analytical and Bioanalytical Chemistry·Tetsuya OsakaHironori Iida
Jul 10, 2012·Chemical Society Reviews·Katsuhiko ArigaHiroshi Tsukube
Jun 10, 2010·Journal of Pharmaceutical Sciences·Aniruddh Singh, Allan S Myerson
Dec 11, 2007·Journal of Colloid and Interface Science·Eleftheria K KodonaPhilippos J Pomonis
Apr 7, 2007·Journal of Colloid and Interface Science·David H Dressler, Yitzhak Mastai
Feb 3, 2007·Physical Chemistry Chemical Physics : PCCP·Marco BieriThomas Bürgi
Feb 8, 2006·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Marco Bieri, Thomas Bürgi
Oct 21, 2015·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Xianbo ZhouJie Liu
Oct 24, 2008·Langmuir : the ACS Journal of Surfaces and Colloids·Paweł SzabelskiMateusz Drach
Jul 26, 2014·Journal of the American Chemical Society·Meng LiXiaogang Qu
Oct 13, 2006·Journal of the American Chemical Society·Takuya NakanishiTetsuya Osaka

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