[formula omitted] 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

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 comple...

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Bibliographic Details
Published inTetrahedron Vol. 55; no. 13; pp. 3883 - 3892
Main Authors Ishi-i, Tsutomu, Iguchi, Ritsuko, Shinkai, Seiji
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 01.03.1999
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Summary: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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(99)00117-9