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Related Concept Videos

Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

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This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
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Disubstituted Cyclohexanes: cis-trans Isomerism02:37

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Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
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Stereoisomerism of Cyclic Compounds02:33

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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Inhibition of Cdk Activity02:34

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The orderly progression of the cell cycle depends on the activation of Cdk protein by binding to its cyclin partner. However, the cell cycle must be restricted when undergoing abnormal changes. Most cancers correlate to the deregulated cell cycle, and since Cdks are a central component of the cell cycle, Cdk inhibitors are extensively studied to develop anticancer agents. For instance, cyclin D associates with several Cdks, such as Cdk 4/6, to form an active complex. The cyclin D-Cdk4/6 complex...
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Structure-Activity Relationships and Drug Design01:28

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Drug design is a dynamic field that involves discovering and developing new medications based on specific biological targets. This process heavily relies on structure-activity relationships (SAR) and quantitative structure-activity relationships (QSAR) to guide the design and optimization of efficient drugs.
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Prochirality02:05

Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Evaluating the experiences of Vietnamese university students enrolled in a longitudinal research cohort: a journey mapping approach.

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Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
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Deciphering the Relationship Between Cycloheximides Structures and Their Different Biological Activities.

Hang Thi Thu Nguyen1, Jae Deok Kim2, Vinit Raj3

  • 1Department of Agricultural Chemistry, College of Agriculture and Life Science, Institute of Environmentally Friendly Agriculture, Chonnam National University, Gwangju, South Korea.

Frontiers in Microbiology
|April 26, 2021
PubMed
Summary
This summary is machine-generated.

Cycloheximide derivatives from Streptomyces sp. JCK-6092 show potent antifungal and phytotoxic activities. Molecular docking reveals their mechanisms, suggesting potential as novel fungicides and herbicides.

Keywords:
antifungal activitycycloheximidesmolecular dockingphytotoxicitystreptomyces

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Area of Science:

  • Microbiology and Natural Product Chemistry
  • Biochemistry and Molecular Biology
  • Agrochemical Science

Background:

  • Streptomyces species are prolific producers of bioactive metabolites, including antifungal and phytotoxic compounds.
  • Cycloheximide (CH) and its derivatives are known protein synthesis inhibitors, but their precise mechanisms and comparative activities are not fully understood.
  • Understanding the differential activities of these compounds is crucial for developing new agrochemicals.

Purpose of the Study:

  • To isolate and compare the antifungal and phytotoxic activities of cycloheximide (CH), acetoxycycloheximide (ACH), and hydroxycycloheximide (HCH).
  • To investigate the molecular mechanisms underlying the biological activities of these cycloheximide derivatives using computational methods.
  • To explore the potential of CH derivatives as lead molecules for novel fungicides and herbicides.

Main Methods:

  • Isolation of CH and ACH from Streptomyces sp. JCK-6092 fermentation broth.
  • Comparative bioassays for antifungal activity against true fungi and oomycetes, and phytotoxicity against weeds and crops.
  • In vitro assessment of phytotoxicity, including chlorophyll content, electrolyte leakage, and lipid peroxidation.
  • Computational studies including molecular docking and density functional theory to analyze interactions with ribosomal proteins in oomycetes, fungi, and plants.

Main Results:

  • CH demonstrated the strongest antifungal activity against true fungi, while CH and ACH showed similar potent inhibition against oomycetes.
  • ACH exhibited the strongest phytotoxic activity, surpassing glufosinate-ammonium and approaching paraquat in efficacy.
  • Molecular docking and DFT analyses correlated binding energies and structural features with observed biological activities, elucidating differential mechanisms of protein synthesis inhibition.

Conclusions:

  • Cycloheximide derivatives possess significant antifungal and phytotoxic properties with distinct activity profiles.
  • Computational studies provide insights into the structure-activity relationships and mechanisms of action, supporting experimental findings.
  • These findings highlight the potential of cycloheximide derivatives as valuable lead compounds for the development of next-generation agrochemicals, particularly fungicides and herbicides.