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

Biosynthesis of Lipids01:29

Biosynthesis of Lipids

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 pathway, which...
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Isomerism in Alkenes02:01

Isomerism in Alkenes

Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
Nomenclature of Alkenes02:29

Nomenclature of Alkenes

The IUPAC naming system for alkenes replaces -an- with -en- in the corresponding parent alkanes. Accordingly, a simple alkene replaces the -ane suffix of the alkane with -ene.
As per the IUPAC rules, the longest carbon chain containing the maximum number of double bonds is identified as the parent chain and is numbered such that the doubly bonded carbon atoms receive the lowest possible numbers. The location of the double bond is indicated by the number of its first carbon atom. In branched...
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

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 alkylated β-keto acid.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

You might also read

Related Articles

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

Sort by
Same author

Functional chararacterization of the enzymes TabB and TabD involved in tabtoxin biosynthesis by Pseudomonas syringae.

Biochemical and biophysical research communications·2018
Same author

ORF7 from Amycolatopsis orientalis catalyzes decarboxylation of N<sup>δ</sup>-methylarginine and amine oxidation of arginine: Biosynthetic implications.

Biochimica et biophysica acta. Proteins and proteomics·2016
Same author

A ketoreductase domain in the PksJ protein of the bacillaene assembly line carries out both alpha- and beta-ketone reduction during chain growth.

Proceedings of the National Academy of Sciences of the United States of America·2008
Same author

Polyunsaturated fatty-acid-like trans-enoyl reductases utilized in polyketide biosynthesis.

Journal of the American Chemical Society·2008
Same author

Incorporation of nonmethyl branches by isoprenoid-like logic: multiple beta-alkylation events in the biosynthesis of myxovirescin A1.

Chemistry & biology·2007
Same author

FenF: servicing the Mycosubtilin synthetase assembly line in trans.

Chembiochem : a European journal of chemical biology·2007

Related Experiment Video

Updated: Jun 30, 2026

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

Isoprenoid-like alkylations in polyketide biosynthesis.

Christopher T Calderone1

  • 1Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, 240 Longwood Avenue, Boston, MA 02115, USA. ccalder2@macalester.edu

Natural Product Reports
|September 30, 2008
PubMed
Summary

A newly discovered polyketide alkylation pathway creates complex beta-branched structures. This pathway parallels isoprenoid biosynthesis, expanding the diversity of accessible polyketide natural products.

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

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Related Experiment Videos

Last Updated: Jun 30, 2026

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

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

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Area of Science:

  • Biochemistry
  • Natural Product Biosynthesis
  • Metabolic Engineering

Background:

  • Polyketides are structurally diverse secondary metabolites produced by iterative Claisen condensation.
  • Current polyketide biosynthesis knowledge primarily focuses on linear chain assembly.
  • Access to branched polyketide structures remains limited.

Purpose of the Study:

  • To describe a newly characterized polyketide alkylation pathway.
  • To highlight parallels between this pathway and isoprenoid biosynthesis.
  • To explore the structural diversity accessible through this novel route.

Main Methods:

  • Review of recent literature on polyketide biosynthesis.
  • Comparative analysis of enzymatic mechanisms in polyketide and isoprenoid pathways.
  • Bioinformatic analysis of gene clusters associated with beta-branched polyketides.

Main Results:

  • Characterization of a novel enzymatic sequence enabling beta-alkylation in polyketide chains.
  • Identification of mechanistic similarities to prenyltransferases in isoprenoid metabolism.
  • Demonstration of the pathway's capacity to generate a range of beta-branched polyketide scaffolds.

Conclusions:

  • The newly identified alkylation pathway significantly expands the structural repertoire of polyketides.
  • This pathway offers new opportunities for engineering novel polyketide natural products.
  • Understanding this pathway provides insights into the evolution of metabolic pathways.