ArticlePloS one2012
A novel tool for studying auxin-metabolism: the inhibition of grapevine indole-3-acetic acid-amido synthetases by a reaction intermediate analogue.
Article in PloS one, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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16 citing papers in PubMed, 38 citations in OpenAlex.
- GH3 phylogenetic subgroups define divergent routes of auxin inactivation via aspartate and glutamine conjugation.Plant physiology · 2026Article
- The Roles of GRETCHEN HAGEN3 (GH3)-Dependent Auxin Conjugation in the Regulation of Plant Development and Stress Adaptation.Plants (Basel, Switzerland) · 2023Review
- Chemical genetic screening identifies nalacin as an inhibitor of GH3 amido synthetase for auxin conjugation.Proceedings of the National Academy of Sciences of the United States of America · 2022Article
- New Wine in an Old Bottle: Utilizing Chemical Genetics to Dissect Apical Hook Development.Life (Basel, Switzerland) · 2022Review
- Chemical inhibition of the auxin inactivation pathway uncovers the roles of metabolic turnover in auxin homeostasis.Proceedings of the National Academy of Sciences of the United States of America · 2022Article
- Auxin Treatment Enhances Anthocyanin Production in the Non-Climacteric Sweet Cherry (International journal of molecular sciences · 2021Article
- Article
- Harnessing symbiotic plant-fungus interactions to unleash hidden forces from extreme plant ecosystems.Journal of experimental botany · 2020Review
- Chlorinated Auxins-How DoesInternational journal of molecular sciences · 2020Article
- Enhanced Conjugation of Auxin by GH3 Enzymes Leads to Poor Adventitious Rooting in Carnation Stem Cuttings.Frontiers in plant science · 2018Article
- Control of Endogenous Auxin Levels in Plant Root Development.International journal of molecular sciences · 2017Review
- Biotin Protein Ligase Is a Target for New Antibacterials.Antibiotics (Basel, Switzerland) · 2016Review
- Transcriptional Responses in Root and Leaf ofFrontiers in plant science · 2016Article
- Improved Synthesis of Biotinol-5'-AMP: Implications for Antibacterial Discovery.ACS medicinal chemistry letters · 2015Article
- Genome-wide analysis and expression profiling suggest diverse roles of GH3 genes during development and abiotic stress responses in legumes.Frontiers in plant science · 2014Article
- Crystal structure of an indole-3-acetic acid amido synthetase from grapevine involved in auxin homeostasis.The Plant cell · 2012Article
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Authors and funding
6 authors at 3 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
An important process for the regulation of auxin levels in plants is the inactivation of indole-3-acetic acid (IAA) by conjugation to amino acids. The conjugation reaction is catalysed by IAA-amido synthetases belonging to the family of GH3 proteins. Genetic approaches to study the biological significance of these enzymes have been hampered by large gene numbers and a high degree of functional redundancy. To overcome these difficulties a chemical approach based on the reaction mechanism of GH3 proteins was employed to design a small molecule inhibitor of IAA-amido synthetase activity. Adenosine-5'-[2-(1H-indol-3-yl)ethyl]phosphate (AIEP) mimics the adenylated intermediate of the IAA-conjugation reaction and was therefore proposed to compete with the binding of MgATP and IAA in the initial stages of catalysis. Two grapevine IAA-amido synthetases with different catalytic properties were chosen to test the inhibitory effects of AIEP in vitro. GH3-1 has previously been implicated in the grape berry ripening process and is restricted to two amino acid substrates, whereas GH3-6 conjugated IAA to 13 amino acids. AIEP is the most potent inhibitor of GH3 enzymes so far described and was shown to be competitive against MgATP and IAA binding to both enzymes with K(i)-values 17-68-fold lower than the respective K(m)-values. AIEP also exhibited in vivo activity in an ex planta test system using young grape berries. Exposure to 5-20 µM of the inhibitor led to decreased levels of the common conjugate IAA-Asp and reduced the accumulation of the corresponding Asp-conjugate upon treatment with a synthetic auxin. AIEP therefore represents a novel chemical probe with which to study IAA-amido synthetase function.
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