Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

4.9K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
4.9K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.1K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
5.1K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.0K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.0K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

12.7K
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.
For example, in...
12.7K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

3.8K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
3.8K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

π-Extended Salphen Scaffolds Enable CO<sub>2</sub> Electroreduction and Singlet Oxygen Generation.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same author

Development and validation of a nomogram model for predicting the risk of failed manual reduction in distal radius fractures.

Frontiers in surgery·2026
Same author

Failed Attempts at Oxidation of XeF<sub>6</sub>: Synthesis and Characterization of [Xe<sub>2</sub>F<sub>11</sub>][RuF<sub>6</sub>].

Inorganic chemistry·2026
Same author

Dual Activation of H<sub>2</sub> and CO<sub>2</sub> by a Pincer-Type Ni-Zn Heterobimetallic Complex.

Angewandte Chemie (International ed. in English)·2026
Same author

Artificial Intelligence-Assisted Confocal Laser Endomicroscopy for Predicting Invasion Depth of Superficial Esophageal Mucosal Lesions: A Cohort Study.

Clinical and translational gastroenterology·2026
Same author

White-light powered autonomous molecular ratchet drives Pd<sup>II</sup> capsules out of equilibrium.

Chemical science·2026

Related Experiment Video

Updated: Jul 13, 2025

A High-Yield Streptomyces Transcription-Translation Toolkit for Synthetic Biology and Natural Product Applications
07:59

A High-Yield Streptomyces Transcription-Translation Toolkit for Synthetic Biology and Natural Product Applications

Published on: September 10, 2021

4.1K

Subrutilane-A Hexacyclic Sesterterpene from Streptomyces subrutilus.

Binbin Gu1, Bernd Goldfuss2, Gregor Schnakenburg3

  • 1Kekulé-Institute for Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121, Bonn, Germany.

Angewandte Chemie (International Ed. in English)
|October 17, 2023
PubMed
Summary

Researchers discovered subrutilane, a novel saturated hexacyclic sesterterpene hydrocarbon, from Streptomyces subrutilus. Its unique structure and formation mechanism were elucidated using advanced analytical and computational methods.

Keywords:
BiosynthesisEnzymesHydrocarbonsIsotopesTerpenes

More Related Videos

From a Natural Product to Its Biosynthetic Gene Cluster: A Demonstration Using Polyketomycin from Streptomyces diastatochromogenes T&#252;6028
09:08

From a Natural Product to Its Biosynthetic Gene Cluster: A Demonstration Using Polyketomycin from Streptomyces diastatochromogenes Tü6028

Published on: January 13, 2017

17.2K
Synthesis and Structure Determination of &#181;-Conotoxin PIIIA Isomers with Different Disulfide Connectivities
11:44

Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities

Published on: October 2, 2018

12.6K

Related Experiment Videos

Last Updated: Jul 13, 2025

A High-Yield Streptomyces Transcription-Translation Toolkit for Synthetic Biology and Natural Product Applications
07:59

A High-Yield Streptomyces Transcription-Translation Toolkit for Synthetic Biology and Natural Product Applications

Published on: September 10, 2021

4.1K
From a Natural Product to Its Biosynthetic Gene Cluster: A Demonstration Using Polyketomycin from Streptomyces diastatochromogenes T&#252;6028
09:08

From a Natural Product to Its Biosynthetic Gene Cluster: A Demonstration Using Polyketomycin from Streptomyces diastatochromogenes Tü6028

Published on: January 13, 2017

17.2K
Synthesis and Structure Determination of &#181;-Conotoxin PIIIA Isomers with Different Disulfide Connectivities
11:44

Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities

Published on: October 2, 2018

12.6K

Area of Science:

  • Natural Product Chemistry
  • Biocatalysis
  • Organic Synthesis

Background:

  • Terpene synthases are crucial enzymes in natural product biosynthesis, catalyzing complex cyclization reactions.
  • Streptomyces species are known producers of diverse secondary metabolites, including terpenes.

Observation:

  • Mining Streptomyces subrutilus yielded a novel hexacyclic sesterterpene, subrutilane, and eight pentacyclic byproducts.
  • Subrutilane is the first identified saturated sesterterpene hydrocarbon.
  • X-ray crystallography and stereoselective deuteration confirmed subrutilane's structure and absolute configuration.

Findings:

  • Isotopic labeling and DFT calculations elucidated the cyclization mechanism for subrutilane and its byproducts.
  • Subrutilane synthase (SrS) also processed (2Z)-geranylfarnesyl pyrophosphate (GFPP) into a major product.
  • Substrate analogues with blocked C6-C7 bonds revealed deviations from the natural cyclization pathway.

Implications:

  • This study expands the known structural diversity of sesterterpenes.
  • Understanding the mechanism of SrS provides insights into terpene biosynthesis and enzyme engineering.
  • The findings contribute to the field of natural product discovery and synthetic biology.