Synthesis of a Novel Rhizobitoxine-Like Triazole-Containing Amino Acid

Boibessot, Thibaut; Bénimèlis, David; Jean, Marion; Benfodda, Zohra; Meffre, Patrick

doi:10.1055/s-0036-1588300

Cited by 9 publications

(2 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Ethylene biosynthesis inhibition by AVG and Rhizobitoxine plays a major role in establishing symbiosis and increasing the nodule number between rhizobacteria and their host legumes (Berkowitz et al, 2006; Boibessot et al, 2016). However, N deprivation or low nitrate concentrations (<50 mg/L = 0.5 mM) are commonly used with AVG treatments to induce nodulation (Xia et al, 2017).…”

Section: Discussionmentioning

confidence: 99%

“…Otherwise, AVG and rhizobitoxine belong to the enol ether family and are a subclass of naturally occurring α-vinylic amino acids (Berkowitz et al, 2006; Boibessot et al, 2016) that are secreted by symbiotic rhizobacteria and pathogenic bacteria (Pruess et al, 1974; Owens et al, 1968; Mitchell et al, 1986; Yasuta et al, 2001). If these two natural compounds at low concentrations (< 5 μM) are known as inhibitors of two enzymes of methionine pathway involved in ethylene biosynthesis: cystathionine β-lyase and ACC synthase (Clausen et al, 1997; Yasuta et al, 1999; Rahman et al, 2000; Berkowitz et al, 2006), the role of their wide inhibitory spectrum on aminotransferases of N metabolism has been neglected in establishing symbiosis and increasing the nodule number (Peters and Crist-Estes, 1989; Xia et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Inhibition of Aminotransferases by Aminoethoxyvinylglycine Triggers a Nitrogen Limitation Condition and Deregulation of Histidine Homeostasis That Impact Root and Shoot Development and Nitrate Uptake

Beauclair²,

Deleu

et al. 2019

Front. Plant Sci.

View full text Add to dashboard Cite

Background and Aims: Although AVG (aminoethoxyvinylglycine) is intensely used to decipher signaling in ethylene/indol-3-acetic acid (IAA) interactions on root morphogenesis, AVG is not a specific inhibitor of aminocyclopropane-1-carboxylate synthase (ACS) and tryptophan aminotransferase (TAA) and tryptophan aminotransferase related (TAR) activities since it is able to inhibit several aminotransferases involved in N metabolism. Indeed, 1 mM glutamate (Glu) supply to the roots in plants treated with 10 μM AVG partially restores the root growth. Here, we highlight the changes induced by AVG and AVG + Glu treatments on the N metabolism impairment and root morphogenetic program. Methods: Root nitrate uptake induced by AVG and AVG + Glu treatments was measured by a differential labeling with 15NO3 - and 15Nglutamate. In parallel a profiling of amino acids (AA) was performed to decipher the impairment of AA metabolism. Key Results: 10 μM AVG treatment increases K15NO3 uptake and 15N translocation during root growth inhibition whereas 10 μM AVG + 1 mM 15Nglutamate treatment inhibits K15NO3 uptake and increases 15Nglutamate uptake during partial root growth restoration. This is explained by a nitrogen (N) limitation condition induced by AVG treatment and a N excess condition induced by AVG + Glu treatment. AA levels were mainly impaired by AVG treatment in roots, where levels of Ser, Thr, α-Ala, β-Ala, Val, Asn and His were significantly increased. His was the only amino acid for which no restoration was observed in roots and shoots after glutamate treatment suggesting important control of His homeostasis on aminotransferase network. Results were discussed in light of recent findings on the interconnection between His homeostasis and the general amino acid control system (GAAC) in eukaryotes. Conclusions: These results demonstrate that AVG concentration above 5 μM is a powerful pharmacological tool for unraveling the involvement of GAAC system or new N sensory system in morphological and metabolic changes of the roots in leguminous and non-leguminous plants.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Inhibition of Aminotransferases by Aminoethoxyvinylglycine Triggers a Nitrogen Limitation Condition and Deregulation of Histidine Homeostasis That Impact Root and Shoot Development and Nitrate Uptake

Beauclair²,

Deleu

et al. 2019

Front. Plant Sci.

View full text Add to dashboard Cite

show abstract

Synthesis and Biological Evaluation of a Library of AGE‐Related Amino Acid Triazole Crosslinkers

et al. 2020

View full text Add to dashboard Cite

Three N‐Boc‐protected amino acids, l‐serine, l‐aspartic, and l‐glutamic acid, were either converted into their methyl azidoalkanoates or various alkynes via Bestmann‐Ohira strategy or via reaction with propargylamine and propargyl bromide, respectively. The Cu‐catalyzed click reaction provided a library of amino acid based triazoles, which were further N‐methylated to triazolium iodides or deprotected and precipitated as free amino acid triazole dihydrochlorides. The biological properties of all derivatives were investigated by cytotoxicity assay (against L929 mouse fibroblasts) and broth microdilution method (E. coli ΔTolC and S. aureus). First results reveal complete inactivity for triazolium iodides with cell viabilities and microbial growths nearly 100 %, indicating them as possible analogs of advanced glycation endproducts (AGEs).

show abstract

The Elaboration of a General Approach to the Asymmetric Synthesis of 1,4‐Substituted 1,2,3‐Triazole Containing Amino Acids via Ni(II) Complexes

et al. 2018

View full text Add to dashboard Cite

Herein we report a general method of the asymmetric synthesis of 1,4‐substituted 1,2,3‐triazole containing amino acids via copper(I) iodide catalyzed “click reaction” between azides and chiral Ni(II) complexes of Schiff bases of (S)‐ or (R)‐BPB with alkyne side chain derivatised amino acids. The final Ni(II) complexes were decomposed with aqueous HCl and the 1,4‐substituted 1,2,3‐triazole containing amino acids isolated with excellent enantioselectivities (>99% ee). The chiral auxiliary ligand (BPB=N‐benzyl proline benzophenone) can be recycled and reused for the synthesis of starting Ni(II) complexes.

show abstract

Synthesis of a Novel Rhizobitoxine-Like Triazole-Containing Amino Acid

Abstract: The synthesis of the four stereoisomers of a new 1,2,3-triazole analogue of rhizobitoxine from serine is described. The key step is a Huisgen 1,3-dipolar cycloaddition on an ethynylglycine synthon.

Cited by 9 publications

References 38 publications

Inhibition of Aminotransferases by Aminoethoxyvinylglycine Triggers a Nitrogen Limitation Condition and Deregulation of Histidine Homeostasis That Impact Root and Shoot Development and Nitrate Uptake

Inhibition of Aminotransferases by Aminoethoxyvinylglycine Triggers a Nitrogen Limitation Condition and Deregulation of Histidine Homeostasis That Impact Root and Shoot Development and Nitrate Uptake

Synthesis and Biological Evaluation of a Library of AGE‐Related Amino Acid Triazole Crosslinkers

The Elaboration of a General Approach to the Asymmetric Synthesis of 1,4‐Substituted 1,2,3‐Triazole Containing Amino Acids via Ni(II) Complexes

Contact Info

Product

Resources

About