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 journalArticlepeer-review

42 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

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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