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Synthesis of a cytokinin linked by a spacer to dexamethasone and biotin: conjugates to detect cytokinin-binding proteins

Journal Article


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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.

UOW Authors


  •   Wang, You (external author)
  •   Letham, David S. (external author)
  •   John, Peter C. L. (external author)
  •   Zhang, Ren

Publication Date


  • 2016

Citation


  • Wang, Y., Letham, D., John, P. C. L. & Zhang, R. (2016). Synthesis of a cytokinin linked by a spacer to dexamethasone and biotin: conjugates to detect cytokinin-binding proteins. Molecules, 21 (5), 576-1-576-14.

Scopus Eid


  • 2-s2.0-84973582949

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=4883&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3860

Start Page


  • 576-1

End Page


  • 576-14

Volume


  • 21

Issue


  • 5

Place Of Publication


  • Switzerland

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.

UOW Authors


  •   Wang, You (external author)
  •   Letham, David S. (external author)
  •   John, Peter C. L. (external author)
  •   Zhang, Ren

Publication Date


  • 2016

Citation


  • Wang, Y., Letham, D., John, P. C. L. & Zhang, R. (2016). Synthesis of a cytokinin linked by a spacer to dexamethasone and biotin: conjugates to detect cytokinin-binding proteins. Molecules, 21 (5), 576-1-576-14.

Scopus Eid


  • 2-s2.0-84973582949

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=4883&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3860

Start Page


  • 576-1

End Page


  • 576-14

Volume


  • 21

Issue


  • 5

Place Of Publication


  • Switzerland