Chiral discrimination of monosaccharides by monolayers of a steroidal boronic acid
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 4,p. 697-702
- https://doi.org/10.1039/p29940000697
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.Keywords
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