Chiral discrimination of monosaccharides by monolayers of a steroidal boronic acid

Reference:

Ludwig, R., Harada, T., Ueda, K., James, T. D. and Shinkai, S., 1994. Chiral discrimination of monosaccharides by monolayers of a steroidal boronic acid. Journal of the Chemical Society, Perkin Transactions 2, 1994 (4), pp. 697-702.

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Official URL:

http://dx.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.

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