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 journalArticle

28 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 languageEnglish
Pages (from-to)697-702
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number4
Publication statusPublished - Dec 1 1994
Externally publishedYes

Fingerprint

Boronic Acids
Monosaccharides
Monolayers
Phase transitions
Compressibility
Isomers
Molecular structure
Physical properties
Cholesterol
Water
Air

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Chiral discrimination of monosaccharides by monolayers of a steroidal boronic acid. / Ludwig, Rainer; Harada, Takaaki; Ueda, Keiko; James, Tony D.; Shinkai, Seiji.

In: Journal of the Chemical Society, Perkin Transactions 2, No. 4, 01.12.1994, p. 697-702.

Research output: Contribution to journalArticle

Ludwig, Rainer ; Harada, Takaaki ; Ueda, Keiko ; James, Tony D. ; Shinkai, Seiji. / Chiral discrimination of monosaccharides by monolayers of a steroidal boronic acid. In: Journal of the Chemical Society, Perkin Transactions 2. 1994 ; No. 4. pp. 697-702.
@article{a43a84b88c64478d9f603c9c917faea3,
title = "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.",
author = "Rainer Ludwig and Takaaki Harada and Keiko Ueda and James, {Tony D.} and Seiji Shinkai",
year = "1994",
month = "12",
day = "1",
language = "English",
pages = "697--702",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
issn = "1470-1820",
publisher = "Royal Society of Chemistry",
number = "4",

}

TY - JOUR

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 - 1994/12/1

Y1 - 1994/12/1

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.

UR - http://www.scopus.com/inward/record.url?scp=37049066522&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37049066522&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:37049066522

SP - 697

EP - 702

JO - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

SN - 1470-1820

IS - 4

ER -