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

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.3K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.3K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

3.9K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
3.9K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

10.1K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
10.1K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

3.7K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
3.7K
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

4.5K
Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
4.5K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

10.1K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.1K

You might also read

Related Articles

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

Sort by
Same author

Simultaneous measurement of piperacillin, tazobactam and meropenem in patient samples using LC-MS/MS to support β-lactam therapeutic drug monitoring.

Analytical methods : advancing methods and applications·2026
Same author

Risk assessment for condylar stress fracture in elite racing Thoroughbreds using standing computed tomography-based virtual mechanical testing.

Equine veterinary journal·2026
Same author

Quantitative Lateral Flow Assay for Meropenem Determination: A Proof-of-Concept Study.

ACS omega·2025
Same author

Oriented Electric Fields─Universal Catalysts.

Accounts of chemical research·2025
Same author

LBONet: Supervised Spectral Descriptors for Shape Analysis.

IEEE transactions on pattern analysis and machine intelligence·2025
Same author

Development of a novel quantitative lateral flow assay for vancomycin for therapeutic drug monitoring.

Scientific reports·2025

Related Experiment Video

Updated: Jun 29, 2025

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

6.9K

Rational design of a cyclohexanone dehydrogenase for enhanced α,β-desaturation and substrate specificity.

Warispreet Singh1, Nicola L Brown1, Hannah V McCue2

  • 1Hub for Biotechnology in Build Environment, Department of Applied Sciences, Faculty of Health and Life Sciences, Northumbria University Newcastle upon Tyne NE1 8ST UK gary.black@northumbria.ac.uk.

Chemical Science
|March 29, 2024
PubMed
Summary

Researchers engineered a cyclohexanone dehydrogenase enzyme for green chemistry applications. This enzyme enables selective α,β-desaturation of cyclic compounds, crucial for synthesizing bioactive molecules.

More Related Videos

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

7.4K
Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether
09:21

Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether

Published on: August 17, 2019

9.0K

Related Experiment Videos

Last Updated: Jun 29, 2025

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

6.9K
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

7.4K
Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether
09:21

Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether

Published on: August 17, 2019

9.0K

Area of Science:

  • Biocatalysis and Green Chemistry
  • Enzyme Engineering
  • Structural Biology

Background:

  • Selective α,β-desaturation of cyclic carbonyl compounds is vital for synthesizing steroids and bioactive molecules.
  • Current methods often lack the green chemistry principles desired for sustainable synthesis.
  • Cyclic carbonyl compounds are core structures in many important natural and synthetic molecules.

Purpose of the Study:

  • To elucidate the structure and mechanism of a novel cyclohexanone dehydrogenase (CHD) from Alicycliphilus denitrificans.
  • To engineer the CHD enzyme for enhanced activity, substrate scope, and application in green synthesis.
  • To provide a foundation for rational enzyme design for regioselective α,β-desaturation.

Main Methods:

  • X-ray crystallography to determine the de novo structure of CHD and its complex with cyclohexanone.
  • Enzyme assays to investigate substrate specificity against various cyclic ketones, lactones, and lactams.
  • Molecular dynamic simulations to guide protein engineering efforts for improved enzyme functionality.

Main Results:

  • The de novo structure of Alicycliphilus denitrificans CHD was solved, revealing active site interactions and cofactor proximity.
  • A Y195F variant provided insights into substrate binding and mechanistic roles of active site residues.
  • Engineered W113A variant exhibited improved activity and accepted bulkier substrates like dihydrocoumarin due to an altered active site.

Conclusions:

  • The engineered CHD enzyme offers a promising biocatalytic tool for regioselective α,β-desaturation.
  • Structural and mechanistic insights facilitate rational design of enzymes for green synthesis.
  • This work enables the bespoke synthesis of valuable bioactive molecules through enzyme engineering.