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

Takuya Nakanishi·Naoko Yamakawa·Toru Asahi·Norio Shibata·Bunsho Ohtani·Tetsuya Osaka
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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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Carboxylic AcidsGoldStereoisomerismThalidomideJournal ArticleResearch Support, Non-U.S. Gov't

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Takuya Nakanishi, Naoko Yamakawa, Toru Asahi, Norio Shibata, Bunsho Ohtani, Tetsuya Osaka. 2004. Chiral discrimination between thalidomide enantiomers using a solid surface with two-dimensional chirality.. https://doi.org/10.1002/chir.20039

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