The Preparation of Solid-Supported Peptide Boronic Acids Derived from 4-Borono-l-phenylalanine and their Affinity for Alizarin

Peter J. Duggan; Daniel A. Offermann

doi:10.1071/CH07143

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The Preparation of Solid-Supported Peptide Boronic Acids Derived from 4-Borono-l-phenylalanine and their Affinity for Alizarin

Peter J. Duggan ^A ^B ^D and Daniel A. Offermann ^C

+ Author Affiliations

- Author Affiliations

^A School of Chemistry, Monash University, Clayton VIC 3800, Australia.

^B CSIRO Molecular and Health Technologies, Bag 10, Clayton South VIC 3169, Australia.

^C Centre for Green Chemistry, Monash University, Clayton VIC 3800, Australia.

^D Corresponding author. Email: peter.duggan@csiro.au

Australian Journal of Chemistry 60(11) 829-834 https://doi.org/10.1071/CH07143
Submitted: 2 May 2007 Accepted: 28 June 2007 Published: 1 November 2007

Abstract

A library of solid-supported pentapeptide diboronic acids, a ‘lysine series’ and an ‘arginine series’, has been efficiently prepared using N-Fmoc-4-pinacolatoborono-l-phenylalanine and standard solid phase peptide synthesis methods. A technique for measuring the affinity of the chromophoric diol, alizarin, to the solid-supported peptide boronic acids has been developed. Considerable variation in alizarin binding strengths, both within and between arginine and lysine series was observed, with association constants in the range 200–1100 M^–1 being recorded. The selective binding characteristics of these boronic acid–peptide hybrids suggest their potential use in carbohydrate sensors and cell-specific diagnostics and therapeutics.

Acknowledgements

The authors thank Professor Bradley Smith, University of Notre Dame, for much valuable advice provided throughout the course of this research, and Dr Ian James, formerly of Mimotopes, for assistance with peptide synthesis. The Australian Research Council and Monash University are thanked for funding.

References

The Preparation of Solid-Supported Peptide Boronic Acids Derived from 4-Borono-l-phenylalanine and their Affinity for Alizarin

Abstract

Acknowledgements

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