Tyrosinases in Organic Chemistry: A Versatile Tool for the α‐Arylation of β‐Dicarbonyl Compounds

Krug, Roxanne; Schröder, Dennis; Gebauer, Jan; Suljić, Sanel; Morimoto, Yoshinari; Fujieda, Nobutaka; Itoh, Shinobu; Pietruszka, Jörg

doi:10.1002/ejoc.201800188

Cited by 7 publications

(5 citation statements)

References 39 publications

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“…SA, BTH and wettable powder are commercially available and Tyr020 has been synthesized according to Krug et al [ 23 ]. Krug et al published this compound under the name compound 8a [ 23 ]. SA, BTH, Tyr020 and wettable powder were diluted in distilled water according to the indicated concentrations.…”

Section: Methodsmentioning

confidence: 99%

“…In this study, we present the setup for a LED-µRAMOS combination and a standard procedure for the identification of new PrimACs on plant seedlings. For a proof-of-principle of the introduced LED-µRAMOS combination and the standard procedure, a model screening for PrimACs has been performed using the newly synthesized methyl 1-(3,4-dihydroxyphenyl)-2-oxocyclopentane-1-carboxylate (Tyr020) as model test compound, which has been introduced by Krug et al [ 23 ]. The power of the novel devise has been shown using SA as a positive control and spotting Tyr020 as a novel PrimAC in A. thaliana .…”

Section: Introductionmentioning

confidence: 99%

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An illuminated respiratory activity monitoring system identifies priming-active compounds in plant seedlings

et al. 2021

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Background Growing large crop monocultures and heavily using pesticides enhances the evolution of pesticide-insensitive pests and pathogens. To reduce pesticide use in crop cultivation, the application of priming-active compounds (PrimACs) is a welcome alternative. PrimACs strengthen the plant immune system and could thus help to protect plants with lower amounts of pesticides. PrimACs can be identified, for example, by their capacity to enhance the respiratory activity of parsley cells in culture as determined by the oxygen transfer rate (OTR) using the respiration activity monitoring system (RAMOS) or its miniaturized version, µRAMOS. The latter was designed for with suspensions of bacteria and yeast cells in microtiter plates (MTPs). So far, RAMOS or µRAMOS have not been applied to adult plants or seedlings, which would overcome the limitation of (µ)RAMOS to plant suspension cell cultures. Results In this work, we introduce a modified µRAMOS for analysis of plant seedlings. The novel device allows illuminating the seedlings and records the respiratory activity in each well of a 48-well MTP. To validate the suitability of the setup for identifying novel PrimAC in Arabidopsis thaliana, seedlings were grown in MTP for seven days and treated with the known PrimAC salicylic acid (SA; positive control) and the PrimAC candidate methyl 1-(3,4-dihydroxyphenyl)-2-oxocyclopentane-1-carboxylate (Tyr020). Twenty-eight h after treatment, the seedlings were elicited with flg22, a 22-amino acid peptide of bacterial flagellin. Upon elicitation, the respiratory activity was monitored. The evaluation of the OTR course reveals Tyr020 as a likely PrimAC. The priming-inducing activity of Tyr020 was confirmed using molecular biological analyses in A. thaliana seedlings. Conclusion We disclose the suitability of µRAMOS for identifying PrimACs in plant seedlings. The difference in OTR during a night period between primed and unprimed plants was distinguishable after elicitation with flg22. Thus, it has been shown that the µRAMOS device can be used for a reliable screening for PrimACs in plant seedlings.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

An illuminated respiratory activity monitoring system identifies priming-active compounds in plant seedlings

et al. 2021

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“…SAR is a broad-spectrum immune response that is induced by salicylic acid (SA) and N-hydroxypipecolic acid (Ryals et al 1996;Delany et al 1994). Thus, upon treatment with N-hydroxypipecolic acid, SA or substances with a similar mode of action, plant cells are frequently primed for the enhanced activation of defense responses (Kauss et al, 1992;Thulke et al 2015) and this usually comes with the establishment of SAR (Conrath et al, 2015 Krug et al (2018). The power of the novel devise has been shown using SA as a positive control and spotting Tyr020 as a novel PrimAC in A. thaliana.…”

Section: Introductionmentioning

confidence: 99%

“…ChemicalsSA and BHT are commercially available and Tyr020 has been synthesized according toKrug et al(2018).Krug et al published this compound under the name compound 8a(Krug et al 2018) …”

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confidence: 99%

An Illuminated Respiratory Activity Monitoring System Identifies Priming-Active Compounds in Plant Seedlings

Loogen

Müller

Balzer

et al. 2021

Preprint

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Background Growing large crop monocultures and heavily using pesticides enhances the chance of evolution of pesticide-insensitive pests and pathogens. To reduce pesticide use in crop cultivation, the application of priming-active compounds (PrimACs) is a welcome alternative. PrimACs strengthen the plant immune system and can thus help to protect plants with lower amounts of pesticides. PrimACs can be identified, for example, by their capacity to enhance the respiratory activity of parsley cells in culture as determined by the oxygen transfer rate (OTR) using the respiration activity monitoring system (RAMOS) or its miniaturized version, µRAMOS. The latter was designed for with suspensions of bacteria and yeast cells in microtiter plates (MTPs). So far, RAMOS or µRAMOS have not been applied to adult plants or seedlings which would overcome the limitation of (µ)RAMOS to plant suspension cell cultures. Results In this work, we introduce a modified µRAMOS for analysis of plant seedlings. The novel device allows illuminating the seedlings and records the respiratory activity in each well of a 48-well MTP. To validate the suitability of the setup for identifying novel PrimAC in Arabidopsis thaliana, seedlings were grown in MTP for seven days and treated with the known PrimAC salicylic acid (SA; positive control) and the PrimAC candidate methyl 1-(3,4-dihydroxyphenyl)-2-oxocyclopentane-1-carboxylate (Tyr020). Twenty-eight h after treatment, the seedlings were elicited with flg22, a 22-amino acid peptide of bacterial flagellin. Upon elicitation, the respiratory activity was monitored. The evaluation of the OTR course reveals Tyr020 as a likely PrimAC. The priming-inducing activity of Tyr020 was confirmed using molecular biological analyses in A. thaliana seedlings. Conclusion We disclose the suitability of µRAMOS for identifying PrimACs in plant seedlings. The difference in OTR during a night period between primed and unprimed plants was clearly distinguishable after elicitation with flg22. Thus, it has been shown, that the µRAMOS device can be used for a reliable screening for PrimACs in plant seedlings.

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“…A tyrosinase from Aspergillus oryzae has been shown to be a useful biocatalyst for the α-arylation of β-dicarbonyl compounds and the generation of quaternary carbon centres. 29 The process involves the enzymatic oxidation of phenols to the corresponding quinones that then undergo a 1,4-addition reaction with the βdicarbonyl compound. An examination of the substrate scope showed that electronrich phenols are preferred (Scheme 6).…”

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Hill

Sutherland

2018

Nat. Prod. Rep.

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Tyrosinases in Organic Chemistry: A Versatile Tool for the α‐Arylation of β‐Dicarbonyl Compounds

Cited by 7 publications

References 39 publications

An illuminated respiratory activity monitoring system identifies priming-active compounds in plant seedlings

An illuminated respiratory activity monitoring system identifies priming-active compounds in plant seedlings

An Illuminated Respiratory Activity Monitoring System Identifies Priming-Active Compounds in Plant Seedlings

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