Concise Total Synthesis of Hydrazidomycin A, a Rare Hydrazide Metabolite of <i>Streptomyces atratus</i>

Meyer, Florian; Ueberschaar, Nico; Hertweck, Christian

doi:10.1002/ejoc.201300532

Cited by 7 publications

(4 citation statements)

References 25 publications

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“…Actinomycin, boromycin, cinerubin, esmeraldine A, furanone, chlorothicin, indanomycin, nosiheptide, oleandomycin, rubromycin, clavam (Wink); dactinomycin (Ayuso-Sacido and Genilloud, 2005) 207K14 (S. thermophilus) − − + − + 0 Thermomycin (Schuurmans et al, 1956) 224K14 ( ; leupeptin, trypsin-protease (Kim and Lee, 1996) 69VY14 (S. atratus) + + + − + 4 Atramycin A, ilamycin (Wink); hydrazidomycin A (Meyer et al, 2013); rufomycin A and B (Shibata et al, 1962) 186K14 (S. collinus) + − + + + 3 Ansatrienin A2, fumarylcarboxamido-2,3-diaminopropanoylalanine, mikamycin, alfa-rubromycin (Wink); kirromycin (Pavlidou et al, 2011) + presence of screened gene;absence of screened gene; S -Streptomyces; *https://www.dsmz.de/bacterial diversity/compendium-of-actinobacteria.html…”

Section: )mentioning

confidence: 99%

Soil Amended With Organic Fertilizers as a Source of Actinomycetes With High Potential as Biocontrol Agents

Javoreková¹,

Kovácsová²,

Medo³

et al. 2019

J microb biotech food sci

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MATERIAL AND METHODS Sample collection Actinomycetes were isolated from soil (Haplic Fluvisol) located near Nitra (Slovakia-latitude 48° 31' 35.97'' N, longitude 18° 11' 46.82'' E), one compost, one vermicompost and soil amended with compost or vermicompost. Vermicompost and compost were applied to the soil at a total dose of 20 Mg.ha −1. The applied compost was prepared by mixing straw (11% by dry weightdw), hay (3% by dw), silage (32% by dw), sheep manure (9% by dw), cow manure (34% by dw) and soil from the subsoil (11% by dw). Vermicompost was prepared by mixing the compost (41% by dw), cow manure (20% by dw), peat and forest litter (21% by dw), soil (10% by dw), a compound of grass, straw and hay (6% by dw) and the fill vermin (2% by dw). The fill vermin (older vermicompost) containing earthworms and cocoons of earthworms (70 earthworms dm −3) was added to the compost. The basic chemical and microbial characteristics of soil samples and both composts (Table 1) were determined according to the defined values: oxidizable carbon (Cox) by the Tiurin method, total nitrogen (Nt) by the Kjeldahl distillation method, pH (H2O) and microbial biomass carbon (Cmic), which was determined by the fumigation-extraction method of Vance et al. (1987). Plant diseases caused by pathogenic fungi are a severe problem for agriculture, and some organic fertilizers have shown a suppressive capacity due to the antagonistic action of microbial communities inhabiting those substrates. The purpose of this work was to isolate and identify actinomycetes from soil, compost and vermicompost able to antagonize phytopathogens. In total, out of 352 actinomycetes successfully recovered on Pochon medium and of which were selected representative 22 mycelium forming isolates, which were subjected to morphological and genotypic characterization. Genetic characterization based on 16S rDNA fragment sequencing revealed that, all the actinomycete isolates belong to the genus Streptomyces. The antifungal activity of isolates was tested against eight phytopathogenic fungi, and they were most activated against Rhizoctonia solani, Alternaria tenuissima, Aspergillus niger and Penicillium expansum. Isolates 51VK13 (Streptomyces sampsonii) and 12VK13 (Streptomyces flavovariabilis) isolated from soil amended with vermicompost showed the greatest antagonistic activity. Their bioactive potential was also confirmed by presence of genes for nonribosomal peptide synthetase (NRPS) and polyketide synthase types I and II (PKS-I and PKS-II). It can, therefore, be concluded that soil amended with organic fertilizers such as compost, and in particular vermicompost, provides a lower incidence of phytopathogens, especially fungi. Isolated actinomycetes have also shown high potential for the production of bioactive compounds useful in the control of plant diseases. ARTICLE INFO

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Section: )mentioning

confidence: 99%

Soil Amended With Organic Fertilizers as a Source of Actinomycetes With High Potential as Biocontrol Agents

Javoreková¹,

Kovácsová²,

Medo³

et al. 2019

J microb biotech food sci

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“…In 2013, the Hertweck group conducted Gooßen's condition of ruthenium‐catalyzed hydroamidation of alkynes using phthalic protected hydrazide 236 as the substrate to obtain N ‐enehydrazide 238 [99] . They screened reaction conditions only to obtain the desired Z configuration product 238 in low yield (11 %) [100a] . In subsequent work, they synthesized hydrazidomycin analogs and evaluated their antiproliferative activities [100b] …”

Section: Synthesis Of N‐alkenylhydrazidesmentioning

confidence: 99%

Synthesis of N‐Aryl‐ and N‐Alkenylhydrazides through C(sp²)−N Bond Construction

Lei

Xie

et al. 2021

Eur J Org Chem

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N‐Aryl‐ and N‐alkenylhydrazides, which include a C(sp2)‐N−N motif, have attracted considerable attention not only in biologically active molecules but also because of their extensive technical applications in organic synthesis. C(sp2)−N bond construction protocols using an N‐acylhydrazine or azocarboxylic ester as the hydrazide source provide a powerful route to these compounds. These protocols exhibit different selectivity manner for the C(sp2) moiety and the regioselectivity issue of the N−N bond. This Minireview documents the available methods that have been developed based on different starting materials. The features and drawbacks of each subdivisional methodology are demonstrated.

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“…In the total synthesis of 1, we initially tested a protocol for the regioselectively cross-coupling of tert-butyl carbazates with vinyl halides at the more acidic NHBoc proton as key step. 23 Whereas this route did not lead to the desired products, 14 we were able to generate four Boc derivatives 9 and 20-22 (Scheme 3). The cross-coupling was performed as reported with (E)-as well as (Z)-1-bromoalk-1-enes, yielding the alkenylated products 23-26 in 31-44% yield.…”

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confidence: 96%

“…12,13 To provide synthetic access to this unusual group of natural hydrazides we and others have recently developed protocols for the assembly of hydrazidomycin A (1). [14][15][16] Yet, nothing is known about structure-activity-relationships of the hydrazidomycins.…”

mentioning

confidence: 99%

Synthesis and biological evaluation of hydrazidomycin analogues

Meyer

Ueberschaar

Dahse

et al. 2013

Bioorganic & Medicinal Chemistry Letters

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Concise Total Synthesis of Hydrazidomycin A, a Rare Hydrazide Metabolite of Streptomyces atratus

Cited by 7 publications

References 25 publications

Soil Amended With Organic Fertilizers as a Source of Actinomycetes With High Potential as Biocontrol Agents

Soil Amended With Organic Fertilizers as a Source of Actinomycetes With High Potential as Biocontrol Agents

Synthesis of N‐Aryl‐ and N‐Alkenylhydrazides through C(sp²)−N Bond Construction

Synthesis and biological evaluation of hydrazidomycin analogues

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Concise Total Synthesis of Hydrazidomycin A, a Rare Hydrazide Metabolite of Streptomyces atratus

Cited by 7 publications

References 25 publications

Soil Amended With Organic Fertilizers as a Source of Actinomycetes With High Potential as Biocontrol Agents

Soil Amended With Organic Fertilizers as a Source of Actinomycetes With High Potential as Biocontrol Agents

Synthesis of N‐Aryl‐ and N‐Alkenylhydrazides through C(sp2)−N Bond Construction

Synthesis and biological evaluation of hydrazidomycin analogues

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Product

Resources

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Synthesis of N‐Aryl‐ and N‐Alkenylhydrazides through C(sp²)−N Bond Construction