Biosynthesis, synthetic studies, and biological activities of the jadomycin alkaloids and related analogues

Koning, Charles B. de; Ngwira, Kennedy J.; Rousseau, Amanda L.

doi:10.1016/bs.alkal.2020.02.001

Cited by 12 publications

(8 citation statements)

References 65 publications

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“…Although jadomycin B could not be detected, the related angucyclines l -digitoxosyl-phenanthroviridin described for S. venezuelae ISP5230 ( 24 ) and, in smaller amounts, phenanthroviridin aglycone ( 25 ) were tentatively identified. l -Digitoxosyl-phenanthroviridin was proposed to be the stable degradation product of the jadomycin B analogue with l -lysine incorporated instead of l -isoleucine ( 24 ).…”

Section: Resultsmentioning

confidence: 92%

Targeted Metabolomics and High-Throughput RNA Sequencing-Based Transcriptomics Reveal Massive Changes in the Streptomyces venezuelae NRRL B-65442 Metabolism Caused by Ethanol Shock

et al. 2022

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Section: Resultsmentioning

confidence: 92%

Targeted Metabolomics and High-Throughput RNA Sequencing-Based Transcriptomics Reveal Massive Changes in the Streptomyces venezuelae NRRL B-65442 Metabolism Caused by Ethanol Shock

et al. 2022

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“…Another precursor used in click chemistry was 1-azido-3-chlorobenzene 6, synthesized by reacting 3chlorobenzene with sodium azide in dried DMF or acetone water [22][23][24]. Dried acetone served as a solvent to prevent azide group degradation by water, facilitating efficient acetone removal from the reaction mixture.…”

Section: Resultsmentioning

confidence: 99%

A Click-Chemistry Approach to New, Potentially Substituted Chemical Structure, Synthesis, And In Vitro Antimicrobial, Cytotoxic, And Antifungal Activity of Novel Chromene Derivatives

Sankhe,

Kamble

2023

ijmst

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A group of chromene derivatives, labeled as 4a-c, were produced by a three-step process using sodium carbonate as a catalyst. The experiment used a solvent mixture consisting of 96% ethanol and water, with a volume ratio of 1:5. A successful reaction between the corresponding hydroxyl chromenes derivatives and propargyl bromide resulted in the propargyl ether compounds 5a-c, which are derived from chromene-3-carbonitriles. 4H-chromene-chlorophenyl conjugates 7a-c were produced by 1H-1,2,3-triazole-tethered click chemistry with propargyl ethers 5a-c and 1-azido-2-chlorobenzene. Copper ions were the most effective catalysts for these chemical reactions. The yields of 1H-1,2,3-triazole varied between 75% and 80%. The antimicrobial activity of all three triazoles (a-c) was studied in vitro. In the study conducted by MCC in 2010, four compounds were found to be effective against B. subtilis, four against S. aureus, four against P. aeruginosa, and five against E. coli.

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“…We detected antibacterial activity at 3 μg mL −1 for the non‐methylated 10 , but not for 9 (Table S5), which might suggest a pro‐drug mechanism by the formation of a methyl ester. The identification of WS‐5995 BGC would facilitate future genetic engineering of this class of ring‐cleaved angucycline antibiotics, which is also observed during the biosynthesis of jadomycin [16] …”

Section: Resultsmentioning

confidence: 99%

Investigation of the Molecular Landscape of Bacterial Aromatic Polyketides by Global Analysis of Type II Polyketide Synthases

Chen

Zhang

2022

Angew Chem Int Ed

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Aromatic polyketides biosynthesized by microorganisms are a prominent class of natural products widely used in clinical treatments. Although genome mining approaches have accelerated the discovery of these molecules, the molecular diversity, abundance, and distribution of bacterial aromatic polyketides at a global scale remain elusive. Here, we provide a global atlas of bacterial aromatic polyketides based on large‐scale analysis of type II polyketide synthases. We first established the chain length factor protein as a marker that can predict both chemical class and molecular uniqueness of the biosynthetic product, and analyzed the abundance, taxonomic distribution, estimated structural diversity, and the total number of aromatic polyketides in bacteria. We further show the identification of oryzanaphthopyrans with an unprecedented angular naphthopyran scaffold from a rare actinobacterium by genome mining guided by the global atlas. These results serve as a compass for exploiting the entire type II polyketide synthase‐derived aromatic polyketides in bacteria.

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Biosynthesis, synthetic studies, and biological activities of the jadomycin alkaloids and related analogues

Cited by 12 publications

References 65 publications

Targeted Metabolomics and High-Throughput RNA Sequencing-Based Transcriptomics Reveal Massive Changes in the Streptomyces venezuelae NRRL B-65442 Metabolism Caused by Ethanol Shock

Targeted Metabolomics and High-Throughput RNA Sequencing-Based Transcriptomics Reveal Massive Changes in the Streptomyces venezuelae NRRL B-65442 Metabolism Caused by Ethanol Shock

A Click-Chemistry Approach to New, Potentially Substituted Chemical Structure, Synthesis, And In Vitro Antimicrobial, Cytotoxic, And Antifungal Activity of Novel Chromene Derivatives

Investigation of the Molecular Landscape of Bacterial Aromatic Polyketides by Global Analysis of Type II Polyketide Synthases

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