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

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

3.6K
Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
3.6K
Biosynthesis in Bacteria01:24

Biosynthesis in Bacteria

93
Biosynthesis in bacteria is a fundamental anabolic process that generates essential macromolecules, including proteins, nucleic acids, lipids, and polysaccharides. These macromolecules are critical for cellular growth, replication, and function. The process is tightly regulated and energetically linked to catabolic pathways to ensure optimal resource utilization.Biosynthetic pathways begin with precursor metabolites such as pyruvate, acetyl-CoA, and glucose-6-phosphate derived from glycolysis,...
93
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

2.9K
The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
2.9K
Biosynthesis of Lipids01:29

Biosynthesis of Lipids

82
Microbial membranes exhibit remarkable diversity in lipid composition, reflecting evolutionary adaptations to various environmental conditions. The three domains of life—Bacteria, Archaea, and Eukarya—synthesize membrane lipids through distinct biosynthetic pathways, leading to fundamental structural differences that impact membrane stability, function, and adaptability.Fatty Acid-Based Lipids in Bacteria and EukaryaBacteria and eukaryotes share a common fatty acid biosynthesis...
82
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

1.8K
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
1.8K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.7K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.7K

You might also read

Related Articles

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

Sort by
Same author

Exploring <i>Sm</i>DHODH inhibition: natural products with potential anti-schistosomiasis activity.

In silico pharmacology·2026
Same author

DPP-IV and FAP-α as Targets of Drug Design: A Comparative Structural Analysis of Molecular Features and Biological Implications.

Medicinal chemistry (Shariqah (United Arab Emirates))·2026
Same author

Flower-like WO<sub>3</sub>-modified Vulcan carbon GDEs for photoelectro-Fenton process: Efficient ciprofloxacin degradation and mechanistic insights.

Journal of environmental management·2026
Same author

Development of DNA Aptamers Against <i>Leishmania infantum</i> GP63 Protein for Therapeutic and Diagnostic Applications.

Pharmaceutics·2026
Same author

Seasonal Dynamics of the Essential Oil Constituents from the Aerial Parts of <i>Vernonanthura polyanthes</i> (Asteraceae) and Their Anti-<i>Leishmania infantum</i> Potential: A Multimethodological Approach.

Plants (Basel, Switzerland)·2026
Same author

Chromatographic Method for Determining 6‑Mercaptopurine in Skin Permeation Assays for Assessing Cutaneous Exposure Risk.

ACS omega·2025

Related Experiment Video

Updated: Sep 2, 2025

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

17.3K

Enzyme-Catalyzed Spiroacetal Formation in Polyketide Antibiotic Biosynthesis.

Oksana Bilyk1, Gabriel S Oliveira2, Rafaela M de Angelo3

  • 1Department of Biochemistry, University of Cambridge, 80 Tennis Court Road, Cambridge CB2 1GA, United Kingdom.

Journal of the American Chemical Society
|August 3, 2022
PubMed
Summary

Researchers discovered a novel spiroketal cyclase enzyme essential for forming spiroketals in polyketide biosynthesis. This enzyme is crucial for producing ossamycin and oligomycin, with its structure and catalytic mechanism now elucidated.

More Related Videos

The Logic, Experimental Steps, and Potential of Heterologous Natural Product Biosynthesis Featuring the Complex Antibiotic Erythromycin A Produced Through E. coli
10:41

The Logic, Experimental Steps, and Potential of Heterologous Natural Product Biosynthesis Featuring the Complex Antibiotic Erythromycin A Produced Through E. coli

Published on: January 13, 2013

18.6K
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.3K

Related Experiment Videos

Last Updated: Sep 2, 2025

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

17.3K
The Logic, Experimental Steps, and Potential of Heterologous Natural Product Biosynthesis Featuring the Complex Antibiotic Erythromycin A Produced Through E. coli
10:41

The Logic, Experimental Steps, and Potential of Heterologous Natural Product Biosynthesis Featuring the Complex Antibiotic Erythromycin A Produced Through E. coli

Published on: January 13, 2013

18.6K
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.3K

Area of Science:

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Background:

  • Polyketides are a diverse class of natural products with significant pharmaceutical potential.
  • Spiroacetal (spiroketal) formation is a critical and stereospecific step in the biosynthesis of many polyketides.
  • The enzymes responsible for catalyzing spiroketal formation have remained largely uncharacterized.

Purpose of the Study:

  • To identify and characterize the enzyme responsible for spiroketal formation in ossamycin and oligomycin biosynthesis.
  • To elucidate the structural and catalytic mechanisms of this novel enzyme.

Main Methods:

  • Bioinformatic analysis of biosynthetic gene clusters (BGCs) for ossamycin and oligomycin.
  • Gene deletion studies to assess the role of putative cyclase genes.
  • Protein purification and enzymatic assays.
  • X-ray crystallography to determine enzyme structures.
  • Site-directed mutagenesis to investigate catalytic residues.

Main Results:

  • Identified OssO and OlmO as novel spiroketal cyclases involved in ossamycin and oligomycin biosynthesis, respectively.
  • Deletion of the olmO gene abolished oligomycin production and yielded spiroketal-deficient metabolites.
  • Purified OlmO demonstrated catalytic activity, converting a precursor into oligomycin C.
  • Crystal structures revealed an unusual 10-strand β-barrel fold for both OssO and OlmO.
  • Conserved polar residues within the enzyme cavity were crucial for catalytic activity, suggesting a general acid/base catalysis mechanism.

Conclusions:

  • Spiroketal formation in ossamycin and oligomycin biosynthesis is catalyzed by a novel class of enzymes, spiroketal cyclases.
  • The identified enzymes, OssO and OlmO, share a conserved β-barrel structure and employ general acid/base catalysis.
  • This discovery provides fundamental insights into polyketide biosynthesis and opens avenues for enzyme engineering.