Chiral discrimination of monosaccharides by monolayers of a steroidal boronic acid

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.

Steroids in Molecular Recognition

“…Compound 158b was also used as an enantiomerically selective sensor at the air−water interface 35 Cholesterol derivatives for ion binding ( 158a/b ), for pyranoside recognition ( 159 ), and for photoswitchable gels ( 160 ), prepared by Shinkai and co-workers. − …”

Molecular design of synthetic receptors with dynamic, imprinting, and allosteric functions

“…For example, sugars present in the subphase are easily detected by a change in the π-A isotherm of boronic-acid-appended amphiphiles Ludwig et al, 1993). In a few sophisticated cases, selective recognition and chiral recognition of sugars become possible by using diboronic acid amphiphiles and cholesterol-based boronic acids, respectively (Ludwig et al, 1994a(Ludwig et al, , 1994bDusemund et al, 1995).…”

Immunosensing system for α-fetoprotein through boronate immunoaffinity column in combination with flow injection chemiluminescence

“…7,8 A boronic acid monolayer at the air-water interface could selectively interact with saccharides. [9][10] Boronate groups assembled on metallic particles or electrode surfaces have been used as an active interface for the detection of sugars. For example, the coupling of 3-aminophenylboronic acid with dithiodialiphatic acids on either silver or gold colloids and on gold electrodes, 11 epoxy-boronate mixed functional monolayers, 12 and phenylboronic acid (APBA) monolayers [13][14][15] on gold have been reported for electrochemical sensing of sugars or glycoproteins.…”