First successful molecular design of an artificial Lewis oligosaccharide binding system utilizing positive homotropic allosterism

A. Sugasaki, K. Sugiyasu, M. Ikeda, M. Takeuchi, S. Shinkai

研究成果: ジャーナルへの寄稿記事

90 引用 (Scopus)

抄録

We have designed phenylboronic acid group appended Ce(IV) bis(porphyrinate) double decker 1 and meso - meso linked porphyrin 2, useful for the allosteric binding of biologically important saccharides, Lewis oligosaccharides. Compound 1 binds Lewis oligosaccharides in aqueous media because of the boronic acid-diol interaction, but the complexation event can occur only above the critical concentrations because of the sigmoidal [oligosaccharide] versus [complex] isotherm. Compound 1 has a sufficiently high affinity with Lewis oligosaccharides (K = 105-106 M-2) with Hill coefficients n of 1.8-2.0, and LewisX series and Lewisa series give opposite, symmetrical CD spectra. This is the first example of efficient binding of Lewis oligosaccharides to the artificial receptor, which has become possible by positive homotropic allosterism.

元の言語英語
ページ(範囲)10239-10244
ページ数6
ジャーナルJournal of the American Chemical Society
123
発行部数42
DOI
出版物ステータス出版済み - 10 24 2001

Fingerprint

Oligosaccharides
Artificial Receptors
Boronic Acids
Acids
Porphyrins
Complexation
Isotherms

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

これを引用

First successful molecular design of an artificial Lewis oligosaccharide binding system utilizing positive homotropic allosterism. / Sugasaki, A.; Sugiyasu, K.; Ikeda, M.; Takeuchi, M.; Shinkai, S.

:: Journal of the American Chemical Society, 巻 123, 番号 42, 24.10.2001, p. 10239-10244.

研究成果: ジャーナルへの寄稿記事

Sugasaki, A. ; Sugiyasu, K. ; Ikeda, M. ; Takeuchi, M. ; Shinkai, S. / First successful molecular design of an artificial Lewis oligosaccharide binding system utilizing positive homotropic allosterism. :: Journal of the American Chemical Society. 2001 ; 巻 123, 番号 42. pp. 10239-10244.
@article{0ef314f674ea463a85c42f09d71a6879,
title = "First successful molecular design of an artificial Lewis oligosaccharide binding system utilizing positive homotropic allosterism",
abstract = "We have designed phenylboronic acid group appended Ce(IV) bis(porphyrinate) double decker 1 and meso - meso linked porphyrin 2, useful for the allosteric binding of biologically important saccharides, Lewis oligosaccharides. Compound 1 binds Lewis oligosaccharides in aqueous media because of the boronic acid-diol interaction, but the complexation event can occur only above the critical concentrations because of the sigmoidal [oligosaccharide] versus [complex] isotherm. Compound 1 has a sufficiently high affinity with Lewis oligosaccharides (K = 105-106 M-2) with Hill coefficients n of 1.8-2.0, and LewisX series and Lewisa series give opposite, symmetrical CD spectra. This is the first example of efficient binding of Lewis oligosaccharides to the artificial receptor, which has become possible by positive homotropic allosterism.",
author = "A. Sugasaki and K. Sugiyasu and M. Ikeda and M. Takeuchi and S. Shinkai",
year = "2001",
month = "10",
day = "24",
doi = "10.1021/ja010806e",
language = "English",
volume = "123",
pages = "10239--10244",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "42",

}

TY - JOUR

T1 - First successful molecular design of an artificial Lewis oligosaccharide binding system utilizing positive homotropic allosterism

AU - Sugasaki, A.

AU - Sugiyasu, K.

AU - Ikeda, M.

AU - Takeuchi, M.

AU - Shinkai, S.

PY - 2001/10/24

Y1 - 2001/10/24

N2 - We have designed phenylboronic acid group appended Ce(IV) bis(porphyrinate) double decker 1 and meso - meso linked porphyrin 2, useful for the allosteric binding of biologically important saccharides, Lewis oligosaccharides. Compound 1 binds Lewis oligosaccharides in aqueous media because of the boronic acid-diol interaction, but the complexation event can occur only above the critical concentrations because of the sigmoidal [oligosaccharide] versus [complex] isotherm. Compound 1 has a sufficiently high affinity with Lewis oligosaccharides (K = 105-106 M-2) with Hill coefficients n of 1.8-2.0, and LewisX series and Lewisa series give opposite, symmetrical CD spectra. This is the first example of efficient binding of Lewis oligosaccharides to the artificial receptor, which has become possible by positive homotropic allosterism.

AB - We have designed phenylboronic acid group appended Ce(IV) bis(porphyrinate) double decker 1 and meso - meso linked porphyrin 2, useful for the allosteric binding of biologically important saccharides, Lewis oligosaccharides. Compound 1 binds Lewis oligosaccharides in aqueous media because of the boronic acid-diol interaction, but the complexation event can occur only above the critical concentrations because of the sigmoidal [oligosaccharide] versus [complex] isotherm. Compound 1 has a sufficiently high affinity with Lewis oligosaccharides (K = 105-106 M-2) with Hill coefficients n of 1.8-2.0, and LewisX series and Lewisa series give opposite, symmetrical CD spectra. This is the first example of efficient binding of Lewis oligosaccharides to the artificial receptor, which has become possible by positive homotropic allosterism.

UR - http://www.scopus.com/inward/record.url?scp=0035944469&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035944469&partnerID=8YFLogxK

U2 - 10.1021/ja010806e

DO - 10.1021/ja010806e

M3 - Article

C2 - 11603973

AN - SCOPUS:0035944469

VL - 123

SP - 10239

EP - 10244

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 42

ER -