Remarkably selective saccharide recognition by solid-supported peptide boronic acids

Peter J. Duggan; Daniel A. Offermann

doi:10.1016/j.tet.2008.10.095

Remarkably selective saccharide recognition by solid-supported peptide boronic acids

Peter J. Duggan, Daniel A. Offermann

Research output: Contribution to journal › Article › peer-review

33 Citations (Scopus)

Abstract

The affinity of nine different saccharides to a library of solid-supported pentapeptide diboronic acids was measured using a competitive binding assay, which employed alizarin as the chromophoric indicator. Considerable variation in carbohydrate binding strengths was observed, with association constants in the range 60-5300 M^-1 being recorded. Of particular note was the 7-fold preference for CMP over AMP shown by peptide 1. Enantioselectivity was also observed, with peptide 4 showing an 8.4-fold binding preference for l-glucose over d-glucose. The remarkably selective binding characteristics of these boronic acid-peptide hybrids suggest their potential use in carbohydrate sensors and cell-specific diagnostics and therapeutics.

Original language	English
Pages (from-to)	109-114
Number of pages	6
Journal	Tetrahedron
Volume	65
Issue number	1
DOIs	https://doi.org/10.1016/j.tet.2008.10.095
Publication status	Published - 3 Jan 2009
Externally published	Yes

Keywords

Boronic acids
Boronolectins
Peptides
Sugar recognition

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abstract = "The affinity of nine different saccharides to a library of solid-supported pentapeptide diboronic acids was measured using a competitive binding assay, which employed alizarin as the chromophoric indicator. Considerable variation in carbohydrate binding strengths was observed, with association constants in the range 60-5300 M-1 being recorded. Of particular note was the 7-fold preference for CMP over AMP shown by peptide 1. Enantioselectivity was also observed, with peptide 4 showing an 8.4-fold binding preference for l-glucose over d-glucose. The remarkably selective binding characteristics of these boronic acid-peptide hybrids suggest their potential use in carbohydrate sensors and cell-specific diagnostics and therapeutics.",

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AU - Duggan, Peter J.

AU - Offermann, Daniel A.

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N2 - The affinity of nine different saccharides to a library of solid-supported pentapeptide diboronic acids was measured using a competitive binding assay, which employed alizarin as the chromophoric indicator. Considerable variation in carbohydrate binding strengths was observed, with association constants in the range 60-5300 M-1 being recorded. Of particular note was the 7-fold preference for CMP over AMP shown by peptide 1. Enantioselectivity was also observed, with peptide 4 showing an 8.4-fold binding preference for l-glucose over d-glucose. The remarkably selective binding characteristics of these boronic acid-peptide hybrids suggest their potential use in carbohydrate sensors and cell-specific diagnostics and therapeutics.

AB - The affinity of nine different saccharides to a library of solid-supported pentapeptide diboronic acids was measured using a competitive binding assay, which employed alizarin as the chromophoric indicator. Considerable variation in carbohydrate binding strengths was observed, with association constants in the range 60-5300 M-1 being recorded. Of particular note was the 7-fold preference for CMP over AMP shown by peptide 1. Enantioselectivity was also observed, with peptide 4 showing an 8.4-fold binding preference for l-glucose over d-glucose. The remarkably selective binding characteristics of these boronic acid-peptide hybrids suggest their potential use in carbohydrate sensors and cell-specific diagnostics and therapeutics.

KW - Boronic acids

KW - Boronolectins

KW - Peptides

KW - Sugar recognition

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DO - 10.1016/j.tet.2008.10.095

M3 - Article

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SP - 109

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JO - Tetrahedron

JF - Tetrahedron

IS - 1

ER -

Remarkably selective saccharide recognition by solid-supported peptide boronic acids

Abstract

Keywords

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