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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