Deuteration of Indole Compounds: Synthesis of Deuterated Auxins, Indole-3-acetic Acid-d5 and Indole-3-butyric Acid-d5.
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ABSTRACT:
SUBMITTER: Yamada T
PROVIDER: S-EPMC8340417 | biostudies-literature |
REPOSITORIES: biostudies-literature
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Project description:The phytohormone auxin plays a central role in many aspects of plant growth and development. IAA is the most studied natural auxin that possesses the property of polar transport in plants. Phenylacetic acid (PAA) has also been recognized as a natural auxin for >40 years, but its role in plant growth and development remains unclear. In this study, we show that IAA and PAA have overlapping regulatory roles but distinct transport characteristics as auxins in plants. PAA is widely distributed in vascular and non-vascular plants. Although the biological activities of PAA are lower than those of IAA, the endogenous levels of PAA are much higher than those of IAA in various plant tissues in Arabidopsis. PAA and IAA can regulate the same set of auxin-responsive genes through the TIR1/AFB pathway in Arabidopsis. IAA actively forms concentration gradients in maize coleoptiles in response to gravitropic stimulation, whereas PAA does not, indicating that PAA is not actively transported in a polar manner. The induction of the YUCCA (YUC) genes increases PAA metabolite levels in Arabidopsis, indicating that YUC flavin-containing monooxygenases may play a role in PAA biosynthesis. Our results provide new insights into the regulation of plant growth and development by different types of auxins.
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Project description:Approximately 500 surface sterilized seeds of Arabidopsis seeds (ecotype: Col-0) were sterilely sown on filter disks overlaying solid ½ MS media 1% sucrose, stratified at 4C for 48 h and grown in darkness at 25C for 4 d. Seedlings were gently submerged by application to the plates of the different auxin solutions (made in ethanol carrier; 0.1% final concentration) and at the indicated times (20 min, 40 min, 60 min), the seedlings were lifted from the plate en mass and flash frozen in liquid nitrogen. Keywords: time-course
2003-10-12 | GSE664 | GEO
Project description:Differential distribution of the plant hormone auxin within tissues mediates a variety of developmental processes. Cellular auxin levels are determined by metabolic processes including synthesis, degradation, and (de)conjugation, as well as by auxin transport across the plasma membrane. Whereas transport of free auxins such as naturally occurring indole-3-acetic acid (IAA) is well characterized, little is known about the transport of auxin precursors and metabolites. Here, we identify a mutation in the ABCG37 gene of Arabidopsis that causes the polar auxin transport inhibitor sensitive1 (pis1) phenotype manifested by hypersensitivity to auxinic compounds. ABCG37 encodes the pleiotropic drug resistance transporter that transports a range of synthetic auxinic compounds as well as the endogenous auxin precursor indole-3-butyric acid (IBA), but not free IAA. ABCG37 and its homolog ABCG36 act redundantly at outermost root plasma membranes and, unlike established IAA transporters from the PIN and ABCB families, transport IBA out of the cells. Our findings explore possible novel modes of regulating auxin homeostasis and plant development by means of directional transport of the auxin precursor IBA and presumably also other auxin metabolites.
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Project description:Burkholderia pyrrocinia JK-SH007 is a plant growth-promoting bacteria (PGPB), that can promote the growth of poplar and other trees, and, production of the plant hormone indole-3-acetic acid (IAA) is one of the reasons for this effect. Therefore, the aims of this study were to evaluate the effect of the external environment on the synthesis of IAA by B. pyrrocinia JK-SH007 and to perform a functional analysis of its IAA synthesis pathway. In this study, IAA and its synthetic intermediates indole-3-acetamide (IAM), indole-3-pyruvic acid (IPyA), tryptamine (TAM), and indole-3-acetonitrile (IAN) were detected in B. pyrrocinia JK-SH007 fermentation broth by high-performance liquid chromatography and tandem mass spectrometry (HPLC-MS/MS), and these indolic compounds were also found in the cell-free extraction of B. pyrrocinia JK-SH007, but the genomic analysis of B. pyrrocinia JK-SH007 indicated that IAA biosynthesis was mainly through the IAM and TAM pathways. The effects of L-tryptophan (L-Trp), temperature and pH on the synthesis of IAA were investigated, and the results showed that L-Trp exerted a significant effect on IAA synthesis and that 37°C and pH 7 were the optimal conditions IAA production by B. pyrrocinia JK-SH007. In addition, the protein expression of tryptophan 2-monooxygenase and indoleacetamide hydrolase, which are the key enzymes of the indole acetamide-mediated IAA synthesis pathway, was analyzed, and their activity was verified by substrate feeding experiments. The results revealed the existence of an IAA synthesis pathway mediated by IAM and indicated that this pathway plays a role in B. pyrrocinia JK-SH007. This study lays the foundation for further exploration of the specific pathway and mechanism of IAA synthesis in B. pyrrocinia JK-SH007.
| S-EPMC6848275 | biostudies-literature
Project description:Indole-3-acetic acid (IAA) is the most common plant hormone of the auxin class and regulates various plant growth processes. The present study investigated IAA production by the basidiomycetous yeast Rhodosporidiobolus fluvialis DMKU-CP293 using the one-factor-at-a-time (OFAT) method and response surface methodology (RSM). IAA production was optimized in shake-flask culture using a cost-effective medium containing 4.5% crude glycerol, 2% CSL and 0.55% feed-grade L-tryptophan. The optimized medium resulted in a 3.3-fold improvement in IAA production and a 3.6-fold reduction in cost compared with those obtained with a non-optimized medium. Production was then scaled up to a 15-L bioreactor and to a pilot-scale (100-L) bioreactor based on the constant impeller tip speed (Vtip) strategy. By doing so, IAA was successfully produced at a concentration of 3569.32 mg/L at the pilot scale. To the best of our knowledge, this is the first report of pilot-scale IAA production by microorganisms. In addition, we evaluated the effect of crude IAA on weed growth. The results showed that weed (Cyperus rotundus L.) growth could be inhibited by 50 mg/L of crude IAA. IAA therefore has the potential to be developed as a herbicidal bioproduct to replace the chemical herbicides that have been banned in various countries, including Thailand.
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Project description:Here we describe a unique process that achieves complete defluorination and decomposition of perfluorinated compounds (PFCs) which comprise one of the most recalcitrant and widely distributed classes of toxic pollutant chemicals found in natural environments. Photogenerated hydrated electrons derived from 3-indole-acetic-acid within an organomodified clay induce the reductive defluorination of co-sorbed PFCs. The process proceeds to completion within a few hours under mild reaction conditions. The organomontmorillonite clay promotes the formation of highly reactive hydrated electrons by stabilizing indole radical cations formed upon photolysis, and prevents their deactivation by reaction with protons or oxygen. In the constrained interlayer regions of the clay, hydrated electrons and co-sorbed PFCs are brought in close proximity thereby increasing the probability of reaction. This novel green chemistry provides the basis for in situ and ex situ technologies to treat one of the most troublesome, recalcitrant and ubiquitous classes of environmental contaminants, i.e., PFCs, utilizing innocuous reagents, naturally occurring materials and mild reaction conditions.
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Project description:DT40 cells and a stable DT 40 cell line expressing OsTIR1 (clone 9) were treated with 500µM IAA for 6 hours. This experiment was conducued to see if auxin would induce a specific sets of genes in animal, like it does for plant cells. We didn't observe a significant difference between the mock control and IAA treatments in both DT40 cells and the stable cells.
2009-10-01 | GSE17523 | GEO
Project description:Deuterated arylamines demonstrate great potential for use in optoelectronic devices, but their widespread utility requires a method for large-scale synthesis. The incorporation of these deuterated materials into optoelectronic devices also provides the opportunity for studies of the functioning device using neutron reflectometry based on the difference in the scattering length density between protonated and deuterated compounds. Here we report mild deuteration conditions utilising standard laboratory glassware for the deuteration of: diphenylamine, N-phenylnaphthylamine, N-phenyl-o-phenylenediamine and 1-naphthylamine (via H/D exchange in D2O at 80 °C, catalysed by Pt/C and Pd/C). These conditions were not successful in the deuteration of triphenylamine or N,N-dimethylaniline, suggesting that these mild conditions are not suitable for the deuteration of tertiary arylamines, but are likely to be applicable for the deuteration of other primary and secondary arylamines. The deuterated arylamines can then be used for synthesis of larger organic molecules or polymers with optoelectronic applications.
| S-EPMC6271713 | biostudies-literature
Project description: Not available
| S-EPMC3834970 | biostudies-literature
Project description:This study aimed at the investigation of the mechanisms of acidogenesis, which is a key process during anaerobic digestion. To expose possible bottlenecks, specific activities of the key enzymes of acidification, such as acetate kinase (Ack, 0.23-0.99 U mg(-1) protein), butyrate kinase (Buk, < 0.03 U mg(-1) protein) and butyryl-CoA:acetate-CoA transferase (But, 3.24-7.64 U mg(-1) protein), were determined in cell free extracts of biogas reactor content from three different biogas reactors. Furthermore, the detection of Ack was successful via Western blot analysis. Quantification of corresponding functional genes encoding Buk (buk) and But (but) was not feasible, although an amplification was possible. Thus, phylogenetic trees were constructed based on respective gene fragments. Four new clades of possible butyrate-producing bacteria were postulated, as well as bacteria of the genera Roseburia or Clostridium identified. The low Buk activity was in contrast to the high specific But activity in the analysed samples. Butyrate formation via Buk activity does barely occur in the investigated biogas reactor. Specific enzyme activities (Ack, Buk and But) in samples drawn from three different biogas reactors correlated with ammonia and ammonium concentrations (NH₃ and NH₄(+)-N), and a negative dependency can be postulated. Thus, high concentrations of NH₃ and NH₄(+)-N may lead to a bottleneck in acidogenesis due to decreased specific acidogenic enzyme activities.
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