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

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.3K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.3K
Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction00:56

Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction

2.0K
The reaction between two different carbonyl compounds comprising α hydrogen in the presence of a strong base like lithium diisopropylamide (LDA) to form a crossed aldol product is known as a directed aldol reaction. The directed aldol reaction is depicted in Figure 1.
2.0K
Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

6.9K
Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α...
6.9K
Formation of Lipopolysaccharides01:19

Formation of Lipopolysaccharides

1.1K
Lipopolysaccharides (LPS) are crucial components of the outer membrane of Gram-negative bacteria, serving both structural and functional roles. It contributes to membrane stability and protects bacteria from host immune responses. LPS is composed of three major regions—lipid A, a core oligosaccharide, and an O antigen. The biosynthesis and assembly of LPS involve a highly coordinated set of enzymatic reactions and transport mechanisms. Additionally, LPS is recognized as an endotoxin,...
1.1K
C–C Bond Formation: Aldol Condensation Overview01:10

C–C Bond Formation: Aldol Condensation Overview

11.8K
Aldol condensation is an important route in synthetic organic chemistry used to generate a new carbon–carbon bond under basic or acidic conditions. The aldol condensation reaction presented in Figure 1 constitutes an aldol addition reaction followed by the dehydration process.
11.8K
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

7.6K
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
7.6K

You might also read

Related Articles

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

Sort by
Same author

The genotypic spectrum of complex febrile seizures: insights from high-risk population genetic screening in a pediatric cohort.

Frontiers in neuroscience·2026
Same author

Monoterpenoids from the roots of <i>Paeonia lactiflora</i> Pall. and their neuroprotective activity.

Natural product research·2026
Same author

Kinetics study reveals interconnected relationships of component activities in trifunctional RNA capping enzymes.

The Journal of biological chemistry·2026
Same author

Anti-interferon-γ autoantibody-associated adult-onset immunodeficiency with occult immunological abnormalities and sequential intracellular infections: a case report.

Frontiers in immunology·2026
Same author

Comparative impact of mental and cardiovascular comorbidities on adverse outcomes in people with MS.

Journal of the neurological sciences·2026
Same author

<sup>19</sup>F NMR probes of conformational change in a bifurcating electron transfer flavoprotein.

Biophysical journal·2026
Same journal

Molecular cloning and functional characterization of tyrosine decarboxylase genes from galanthamine-producing Narcissus pseudonarcissus 'King Alfred.'

Phytochemistry·2026
Same journal

Five undescribed compounds isolated from Gerbera delavayi with their anti-inflammatory activity.

Phytochemistry·2026
Same journal

Ingenane diterpenoids with anti-inflammatory activity from the whole plants of Euphorbia peplus.

Phytochemistry·2026
Same journal

Discovery of cytotoxic 1,4-benzodioxane oxyneolignan analogues from Glechoma longituba.

Phytochemistry·2026
Same journal

Cinnamolides A-G, seven previously undescribed phytoconstituents from the peels of Cinnamomum chago and their anti-inflammatory activity.

Phytochemistry·2026
Same journal

Antiviral amide derivatives from Uvaria siamensis.

Phytochemistry·2026
See all related articles

Related Experiment Video

Updated: May 4, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
09:14

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Published on: February 16, 2018

11.3K

Ether bridge formation in loline alkaloid biosynthesis.

Juan Pan1, Minakshi Bhardwaj2, Jerome R Faulkner1

  • 1Department of Plant Pathology, 201F Plant Sciences Building, 1405 Veterans Drive, University of Kentucky, Lexington, KY 40546-0312, USA.

Phytochemistry
|December 31, 2013
PubMed
Summary
This summary is machine-generated.

LolO, a fungal enzyme, is crucial for forming the insecticidal lolines found in grasses. Disrupting LolO leads to the accumulation of exo-1-acetamidopyrrolizidine, a precursor molecule.

Keywords:
ClavicipitaceaeEpichloë spp.Genome sequencingGrass symbiontsLoline alkaloidsOxoglutarate/iron-dependent dioxygenasePyrrolizidinesexo-1-AcetamidopyrrolizidinelolO

More Related Videos

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
07:59

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

Published on: October 4, 2019

11.9K
Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-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

6.0K

Related Experiment Videos

Last Updated: May 4, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
09:14

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Published on: February 16, 2018

11.3K
A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
07:59

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

Published on: October 4, 2019

11.9K
Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-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

6.0K

Area of Science:

  • Biochemistry
  • Mycology
  • Chemical Ecology

Background:

  • Lolines are potent insecticidal alkaloids produced by endophytic fungi in cool-season grasses.
  • These alkaloids feature a pyrrolizidine ring and an unusual ether bridge.
  • 1-aminopyrrolizidine has been previously identified as a potential intermediate in loline biosynthesis.

Purpose of the Study:

  • To investigate the role of the fungal gene lolO in the biosynthesis of lolines.
  • To identify alkaloid intermediates and understand the mechanism of ether bridge formation in loline production.

Main Methods:

  • RNA interference (RNAi) was used to reduce the expression of lolO in endophytic fungi.
  • High-resolution mass spectrometry (MS) and nuclear magnetic resonance (NMR) were employed for alkaloid identification.
  • Genome sequencing of endophytes with varying alkaloid profiles was performed.
  • Heterologous expression of wild-type lolO was used to complement a lolO mutant.

Main Results:

  • Knocking down lolO expression resulted in the accumulation of exo-1-acetamidopyrrolizidine.
  • Fungal endophytes with mutated lolO accumulated exo-1-acetamidopyrrolizidine but not lolines.
  • Heterologous expression of wild-type lolO in a mutant restored the production of N-acetylnorloline.
  • These findings implicate the non-heme iron oxygenase LolO in the formation of the loline ether bridge.

Conclusions:

  • The non-heme iron oxygenase LolO is essential for the formation of the characteristic ether bridge in lolines.
  • LolO likely functions by oxidizing exo-1-acetamidopyrrolizidine to facilitate ether bridge formation.
  • Understanding this pathway provides insights into the biosynthesis of important insecticidal natural products.