Chiral discrimination of monosaccharides by monolayers of a steroidal boronic acid

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

doi:10.1039/p29940000697

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 journal › Article › peer-review

29 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 language	English
Pages (from-to)	697-702
Number of pages	6
Journal	Journal of the Chemical Society, Perkin Transactions 2
Issue number	4
DOIs	https://doi.org/10.1039/p29940000697
Publication status	Published - Jan 1 1994
Externally published	Yes

All Science Journal Classification (ASJC) codes

Chemistry(all)

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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.",

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T1 - Chiral discrimination of monosaccharides by monolayers of a steroidal boronic acid

AU - Ludwig, Rainer

AU - Harada, Takaaki

AU - Ueda, Keiko

AU - James, Tony D.

AU - Shinkai, Seiji

PY - 1994/1/1

Y1 - 1994/1/1

N2 - 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.

AB - 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.

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Chiral discrimination of monosaccharides by monolayers of a steroidal boronic acid

Abstract

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