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

doi:10.1002/chir.20039

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

41 Citations (Scopus)

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-alf of that caused by pure enantiomeric SAM.

Original language	English
Pages (from-to)	S36-S39
Journal	Chirality
Volume	16
Issue number	SUPPL.
DOIs	https://doi.org/10.1002/chir.20039
Publication status	Published - 2004 Aug 3

Keywords

Binaphthalenedithiol
Enantioselective adsorption
Gold(111) surface
Quartz crystal microbalance
Self-assembled monolayer

ASJC Scopus subject areas

Analytical Chemistry
Catalysis
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

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10.1002/chir.20039

Cite this

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AU - Nakanishi, Takuya

AU - Yamakawa, Naoko

AU - Asahi, Toru

AU - Shibata, Norio

AU - Ohtani, Bunsho

AU - Osaka, Tetsuya

PY - 2004/8/3

Y1 - 2004/8/3

N2 - 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-alf of that caused by pure enantiomeric SAM.

AB - 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-alf of that caused by pure enantiomeric SAM.

KW - Binaphthalenedithiol

KW - Enantioselective adsorption

KW - Gold(111) surface

KW - Quartz crystal microbalance

KW - Self-assembled monolayer

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

Abstract

Keywords

ASJC Scopus subject areas

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