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Molecules 2016, 21(5), 576; doi:10.3390/molecules21050576

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
Received: 19 February 2016 / Revised: 25 April 2016 / Accepted: 25 April 2016 / Published: 30 April 2016
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1185 KB, uploaded 30 April 2016]   |  

Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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