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Open AccessArticle

Synthesis of a Cytokinin Linked by a Spacer to Dexamethasone and Biotin: Conjugates to Detect Cytokinin-Binding Proteins

1
School of Biological Sciences, University of Wollongong, Wollongong, NSW 2522, Australia
2
Research School of Biology, Australian National University, Canberra, ACT 0200, Australia
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Molecules 2016, 21(5), 576; https://doi.org/10.3390/molecules21050576
Received: 19 February 2016 / Revised: 25 April 2016 / Accepted: 25 April 2016 / Published: 30 April 2016
(This article belongs to the Section Organic Chemistry)
Yeast cells expressing cDNA libraries have provided two new approaches to facilitate further identification of cytokinin-binding proteins and receptors. These are the yeast three hybrid (Y3H) system and fluorescence activated cell sorting (FACS). The Y3H system requires a synthetic hybrid ligand comprising an “anchor” moiety (e.g., dexamethasone) linked to a cytokinin via a spacer. In the yeast nucleus, this ligand by binding connects two fusion proteins leading to a reporter gene activation and detection and characterisation of cytokinin binding proteins. Herein is reported the first synthesis of dexamethasone-cytokinin ligands with a spacer linkage. This was attached to the purine ring of 6-benzylaminopurine (BAP) at positions 2, 8 or 9. To achieve this, dexamethasone was modified by periodate oxidation yielding a carboxylic group used for conjugation to the spacer by amide formation. Biotinyl derivatives of cytokinins for FACS included those synthesised by reaction of an activated ester of biotin with 8-(10-amino-decylamino) derivatives of BAP and BAP 9-riboside. Properties of the conjugates and some biological situations where they could be applicable are discussed briefly. View Full-Text
Keywords: 6-benzylaminopurine (BAP); BAP-dexamethasone conjugates; BAP-biotin conjugates; yeast three hybrid; cytokinin-binding proteins 6-benzylaminopurine (BAP); BAP-dexamethasone conjugates; BAP-biotin conjugates; yeast three hybrid; cytokinin-binding proteins
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MDPI and ACS Style

Wang, Y.; Letham, D.S.; John, P.C.L.; Zhang, R. Synthesis of a Cytokinin Linked by a Spacer to Dexamethasone and Biotin: Conjugates to Detect Cytokinin-Binding Proteins. Molecules 2016, 21, 576.

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