Chiral discrimination of monosaccharides by monolayers of a steroidal boronic acid

Rainer Ludwig, Takaaki Harada, Keiko Ueda, Tony D. James, Seiji Shinkai

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

The relationship between molecular structure and physical properties of monolayers of complexes between an amphiphilic, steroidal cholesterol- substituted phenylboronic acid (1) and monosaccharides was studied at the air-water interface. Phase transition, compressibility and limiting molecular area of monolayers of 1 in the presence of monosaccharides are correlated with the calculated structures of the phenylboronic acid-monosaccharide complexes. The monolayer of 1 exhibits chiral discrimination towards optical isomers of monosaccharides. The phase transition during compression of monolayers of 1 is discussed to reflect rearranged binding positions between the boronic acid and monosaccharides.

Original languageEnglish
Pages (from-to)697-702
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number4
DOIs
Publication statusPublished - Jan 1 1994
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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