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 journalArticlepeer-review

Abstract

The relationship between molecular structure and physical properties of monolayers of complexes between an amphiphilic, steroidal cholesterol-substituted phenylboronic acid (1) and mono-saccharides 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
Volume1994
Issue number4
DOIs
Publication statusPublished - 1994

Fingerprint Dive into the research topics of 'Chiral discrimination of monosaccharides by monolayers of a steroidal boronic acid'. Together they form a unique fingerprint.

Cite this