D/L selective re-binding of saccharide-imprinted [60]fullerene- bisadducts based on a saccharide-boronic acid interaction: Development of a molecular imprinting technique useful in a homogeneous system

Tsutomu Ishi-i, Ritsuko Iguchi, Seiji Shinkai

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30 Citations (Scopus)

Abstract

The memory effect of the D-threitol- or L-threitol-imprinted [60]fullerene-bisadduct [((f)C)-4 or ((f)A)-4], which was obtained from the double addition reaction between [60]fullerene and D-threitol- or L-threitol- boronic acid 1:2 complex (D-1 or L-1), was discussed. In the competitive complexation with D-threitol and L-threitol, ((f)C)-4 or ((f)A)-4 diastereoselectively rebound with the original template, D-threitol or L- threitol, respectively, affording the corresponding 1:1 complex [((f)C)-3D or ((f)A)-3L]. The selectivities increased with lowering the complexation temperature; under the optimum conditions 48% diastereomeric excess was achieved.

Original languageEnglish
Pages (from-to)3883-3892
Number of pages10
JournalTetrahedron
Volume55
Issue number13
DOIs
Publication statusPublished - Mar 26 1999
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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