Synthesis of a Reversible Streptavidin Binder for Biomimetic Assemblies

Nathan W. Moore; Anthony R. C. Delacruz; Katherine S. Lancaster; Thorsten Dieckmann; Tonya L. Kuhl

doi:10.1071/CH06319

RESEARCH ARTICLE

Synthesis of a Reversible Streptavidin Binder for Biomimetic Assemblies

Nathan W. Moore ^A , Anthony R. C. Delacruz ^A , Katherine S. Lancaster ^B , Thorsten Dieckmann ^C and Tonya L. Kuhl ^A ^D

+ Author Affiliations

- Author Affiliations

^A Department of Chemical Engineering and Materials Science, University of California at Davis, 1 Shields Ave, Davis, CA 95616, USA.

^B Department of Chemistry, University of California at Davis, 1 Shields Ave, Davis, CA 95616, USA.

^C Department of Chemistry, University of Waterloo, 200 University Ave West, Waterloo, ON N2L 3G1, Canada.

^D Corresponding author. Email: tlkuhl@ucdavis.edu

Australian Journal of Chemistry 60(5) 363-368 https://doi.org/10.1071/CH06319
Submitted: 31 August 2006 Accepted: 9 March 2007 Published: 28 May 2007

Abstract

The biotin/streptavidin ligand/receptor pair is used extensively in biotechnology. However, less is known about HABA (2-(4-hydroxyphenylazo)benzoic acid), which binds to streptavidin with a bond energy and dissociation constant that more closely mimics antibody/antigen interactions. In this work we demonstrate some of HABA’s useful properties that may make it a good substitute for biotin in a broad range of biochemical research. Specifically, we investigate its ease of conjugation to an anchoring pegylated lipid, characterization with MALDI, NMR, and visible-wavelength spectroscopies, and incorporation into lipid vesicles.

Acknowledgments

We thank Jordan Kopping, Philip J. Costanzo, and Tim E. Patten for useful discussions, Jeff de Ropp for assistance with NMR, Kaki Cheung and Dennis J. Mulder for writing the spectrometer control software, and Yanto Yanto for help making the vesicles. An NSF Grant NER DMII-0404457 supported this work.

References

Synthesis of a Reversible Streptavidin Binder for Biomimetic Assemblies

Abstract

Acknowledgments

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