The first example of positive allosterism in an aqueous saccharide- binding system designed on a Ce(IV) bis(porphyrinate) double decker scaffold

Atsushi Sugasaki, Masato Ikeda, Masayuki Takeuchi, Kazuya Koumoto, Seiji Shinkai

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

The first example of a positive, homotropic system in aqueous saccharide-binding has been achieved using a Ce(IV) bis(porphyrinate) double decker scaffold bearing two pairs of boronic acid groups (compound 2). In this system, the binding of the first guest (1:2 saccharide/boronic acid complex) suppresses the rotational freedom of the two porphyrin planes, which facilitates the binding of the second guest. As a result, two pairs of boronic acid groups in 2 can autoacceleratively bind these guests and yield CD-active species. The analyses of CD intensity-guest concentration plots according to the Hill equation resulted in K=3.7x104 M-2 and n=2.0 for D- fructose and K=9.6x105 M-2 and n=1.6 for D-glucose. The present system which is in action even in aqueous media is widely applicable to allosteric control of drug release, catalytic reaction, information transduction, etc. of saccharide-containing guest molecules. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)4717-4723
Number of pages7
JournalTetrahedron
Volume56
Issue number27
DOIs
Publication statusPublished - Jun 30 2000

Fingerprint

Boronic Acids
Scaffolds
Bearings (structural)
Porphyrins
Fructose
Glucose
Molecules
Pharmaceutical Preparations

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

The first example of positive allosterism in an aqueous saccharide- binding system designed on a Ce(IV) bis(porphyrinate) double decker scaffold. / Sugasaki, Atsushi; Ikeda, Masato; Takeuchi, Masayuki; Koumoto, Kazuya; Shinkai, Seiji.

In: Tetrahedron, Vol. 56, No. 27, 30.06.2000, p. 4717-4723.

Research output: Contribution to journalArticle

Sugasaki, Atsushi ; Ikeda, Masato ; Takeuchi, Masayuki ; Koumoto, Kazuya ; Shinkai, Seiji. / The first example of positive allosterism in an aqueous saccharide- binding system designed on a Ce(IV) bis(porphyrinate) double decker scaffold. In: Tetrahedron. 2000 ; Vol. 56, No. 27. pp. 4717-4723.
@article{77283dbd0f964aea9bd7875fb2d11575,
title = "The first example of positive allosterism in an aqueous saccharide- binding system designed on a Ce(IV) bis(porphyrinate) double decker scaffold",
abstract = "The first example of a positive, homotropic system in aqueous saccharide-binding has been achieved using a Ce(IV) bis(porphyrinate) double decker scaffold bearing two pairs of boronic acid groups (compound 2). In this system, the binding of the first guest (1:2 saccharide/boronic acid complex) suppresses the rotational freedom of the two porphyrin planes, which facilitates the binding of the second guest. As a result, two pairs of boronic acid groups in 2 can autoacceleratively bind these guests and yield CD-active species. The analyses of CD intensity-guest concentration plots according to the Hill equation resulted in K=3.7x104 M-2 and n=2.0 for D- fructose and K=9.6x105 M-2 and n=1.6 for D-glucose. The present system which is in action even in aqueous media is widely applicable to allosteric control of drug release, catalytic reaction, information transduction, etc. of saccharide-containing guest molecules. (C) 2000 Elsevier Science Ltd.",
author = "Atsushi Sugasaki and Masato Ikeda and Masayuki Takeuchi and Kazuya Koumoto and Seiji Shinkai",
year = "2000",
month = "6",
day = "30",
doi = "10.1016/S0040-4020(00)00395-1",
language = "English",
volume = "56",
pages = "4717--4723",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "27",

}

TY - JOUR

T1 - The first example of positive allosterism in an aqueous saccharide- binding system designed on a Ce(IV) bis(porphyrinate) double decker scaffold

AU - Sugasaki, Atsushi

AU - Ikeda, Masato

AU - Takeuchi, Masayuki

AU - Koumoto, Kazuya

AU - Shinkai, Seiji

PY - 2000/6/30

Y1 - 2000/6/30

N2 - The first example of a positive, homotropic system in aqueous saccharide-binding has been achieved using a Ce(IV) bis(porphyrinate) double decker scaffold bearing two pairs of boronic acid groups (compound 2). In this system, the binding of the first guest (1:2 saccharide/boronic acid complex) suppresses the rotational freedom of the two porphyrin planes, which facilitates the binding of the second guest. As a result, two pairs of boronic acid groups in 2 can autoacceleratively bind these guests and yield CD-active species. The analyses of CD intensity-guest concentration plots according to the Hill equation resulted in K=3.7x104 M-2 and n=2.0 for D- fructose and K=9.6x105 M-2 and n=1.6 for D-glucose. The present system which is in action even in aqueous media is widely applicable to allosteric control of drug release, catalytic reaction, information transduction, etc. of saccharide-containing guest molecules. (C) 2000 Elsevier Science Ltd.

AB - The first example of a positive, homotropic system in aqueous saccharide-binding has been achieved using a Ce(IV) bis(porphyrinate) double decker scaffold bearing two pairs of boronic acid groups (compound 2). In this system, the binding of the first guest (1:2 saccharide/boronic acid complex) suppresses the rotational freedom of the two porphyrin planes, which facilitates the binding of the second guest. As a result, two pairs of boronic acid groups in 2 can autoacceleratively bind these guests and yield CD-active species. The analyses of CD intensity-guest concentration plots according to the Hill equation resulted in K=3.7x104 M-2 and n=2.0 for D- fructose and K=9.6x105 M-2 and n=1.6 for D-glucose. The present system which is in action even in aqueous media is widely applicable to allosteric control of drug release, catalytic reaction, information transduction, etc. of saccharide-containing guest molecules. (C) 2000 Elsevier Science Ltd.

UR - http://www.scopus.com/inward/record.url?scp=0034733554&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034733554&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(00)00395-1

DO - 10.1016/S0040-4020(00)00395-1

M3 - Article

AN - SCOPUS:0034733554

VL - 56

SP - 4717

EP - 4723

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 27

ER -