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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Differences between the structural requirements for ABA 8'-hydroxylase inhibition and for ABA activity.

A major catabolic enzyme of the plant hormone abscisic acid (ABA) is the cytochrome P450 monooxygenase ABA 8'-hydroxylase. For designing a specific inhibitor of this enzyme, the substrate specificity and inhibition of CYP707A3, an ABA 8'-hydroxylase from Arabidopsis thaliana, was investigated using 45 structural analogues of ABA and compared to the structural requirements for ABA activity. Substrate recognition by the enzyme strictly required the 6'-methyl groups (C-8' and C-9'), which were unnecessary for ABA activity, whereas elimination of the 3-methyl (C-6) and 1'-hydroxyl groups, which significantly affected ABA activity, had little effect on the ability of analogues to competitively inhibit the enzyme. Fluorination at C-8' and C-9' resulted in resistance to 8'-hydroxylation and competitive inhibition of the enzyme. In particular, 8',8'-difluoro-ABA and 9',9'-difluoro-ABA yielded no enzyme reaction products and strongly inhibited the enzyme (K(I) = 0.16 and 0.25 microM, respectively).[1]

References

  1. Differences between the structural requirements for ABA 8'-hydroxylase inhibition and for ABA activity. Ueno, K., Araki, Y., Hirai, N., Saito, S., Mizutani, M., Sakata, K., Todoroki, Y. Bioorg. Med. Chem. (2005) [Pubmed]
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