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Title: Enantioselective Synthesis and Chemical Genomics of Abscisic Acid
Author: Smith, Timothy Robert
ISNI:       0000 0001 3467 7448
Awarding Body: University of Warwick
Current Institution: University of Warwick
Date of Award: 2007
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Abscisic acid is an important phytohonnone implicated in many aspects of plant growth and development. The search for the biological targets of this ubiquitous honnone has produced many sophisticated strategies for the preparation of analogues and conjugates for use in affinity-based methods. In this study, biologically active . enantiomerically pure abscisic acid conjugates were synthesised and screened against a phage display library of Arabidopsis thaliana cDNA products in order to identify receptor proteins. A short and high-yielding synthesis of enantiomerically pure S-(+)- and R-(-)abscisic acid are described. The syntheses proceed through key intennediates that preferentially recrystallise as single diastereoisomers for each enantiomer. This versatile route to abscisic acid was adapted for generation of novel side-chain analogues suitable for conjugation and immobilisation. S-(+)-Abscisic acid conjugated to biotin via an acyl hydrazone linkage was assessed for in vivo stability using bioassays twinned with LCMS2 analysis on deuterated samples. Cleavage ofthe otherwise stable acyl hydrazone linkage was observed. Phage display biopanning on immobilised conjugates selected two protein fragments that had high affinity for the immobilised abscisic acid. The corresponding proteins, CBL-interacting protein kinase 6 and Vernalization Independence 5 are likely candidates as abscisic acid binding proteins. Biopanning on a Magic-Tag® immobilised analogue similarly selected for three putative abscisic acid binding proteins: EFS, peptidyl-prolyl cis-trans isomerase and CAXX amino protease.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available