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

Research output: Contribution to journalArticle

36 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 languageEnglish
JournalChirality
Volume16
Issue numberSUPPL.
DOIs
Publication statusPublished - 2004

Fingerprint

Thalidomide
Enantiomers
Chirality
Self assembled monolayers
Gold
Adsorption
Enantioselectivity
dithiol

Keywords

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

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Chiral discrimination between thalidomide enantiomers using a solid surface with two-dimensional chirality. / Nakanishi, Takuya; Yamakawa, Naoko; Asahi, Toru; Shibata, Norio; Ohtani, Bunsho; Osaka, Tetsuya.

In: Chirality, Vol. 16, No. SUPPL., 2004.

Research output: Contribution to journalArticle

Nakanishi, Takuya ; Yamakawa, Naoko ; Asahi, Toru ; Shibata, Norio ; Ohtani, Bunsho ; Osaka, Tetsuya. / Chiral discrimination between thalidomide enantiomers using a solid surface with two-dimensional chirality. In: Chirality. 2004 ; Vol. 16, No. SUPPL.
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