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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Studies Directed Towards the Preparation of Probes for the Photoaffinity Labelling of Gibberellin Receptors

James R. Crow A , Peter M. Chandler B and Lewis N. Mander A C
+ Author Affiliations
- Author Affiliations

A Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.

B CSIRO Plant Industry, GPO Box 1600, Canberra, ACT 2601, Australia.

C Corresponding author. Email: mander@rsc.anu.edu.au

Australian Journal of Chemistry 64(4) 471-488 https://doi.org/10.1071/CH10441
Submitted: 3 December 2010  Accepted: 17 February 2011   Published: 18 April 2011

Abstract

Model studies for the preparation of photoaffinity probes designed to explore the nature of gibberellin receptor sites have provided a wide range of gibberellin derivatives that should afford useful scaffolds incorporating auxiliary groups attached to C-2 and C-12. Methodology features the stereocontrolled opening of 2β,3β-epoxy gibberellins by attack on the lower face at C-2, while functionalization of C-12 was effected by the rhodium acetate-catalyzed CH insertion reaction of a 17-diazo ketone. Compounds were screened for bioactivity in growth and barley endosperm-based bioassays.


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