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

Peptide Bonds02:43

Peptide Bonds

74.5K
A peptide bond covalently attaches amino acids through a dehydration reaction. One amino acid's carboxyl group and another amino acid's amino group combine, releasing a water molecule. The resulting bond is the peptide bond. The products that such linkages form are peptides. As more amino acids join this growing chain, the resulting chain is a polypeptide. Each polypeptide has a free amino group at one end. This end has the N-terminal, or the amino-terminal, and the other end has a free...
74.5K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.5K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
2.5K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

10.2K
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.
10.2K
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

1.9K
Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
1.9K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.6K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
3.6K
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

3.3K
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...
3.3K

You might also read

Related Articles

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

Sort by
Same author

The polyketide-macrolactone phomolide I produced by the endophytic fungus <i>Arthrinium marii</i> M-211.

Natural product research·2026
Same author

Lipidation of a nuclear localization sequence enhances broad-spectrum antimicrobial activity: synthesis, characterization, and in silico analysis.

Artificial cells, nanomedicine, and biotechnology·2026
Same author

Didychaudianin A: a new tirucallane triterpenoid from the stem bark of Indonesian <i>Didymocheton gaudichaudianus</i> (Meliaceae).

Natural product research·2026
Same author

Antimalarial potential of curcumin derivatives evaluated through experimental and computational approaches.

Scientific reports·2025
Same author

Linkers for effective peptide-drug conjugates.

Bioorganic & medicinal chemistry·2025
Same author

Improved albumin binding properties of Isoguvacine upon esterification as characterized by biophysical and computational tools.

Scientific reports·2025

Related Experiment Video

Updated: Jul 7, 2025

Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles PPAs and Related Biomaterials
08:55

Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles PPAs and Related Biomaterials

Published on: June 25, 2018

8.1K

Epimerisation in Peptide Synthesis.

Suleman Duengo1,2, Muhamad Imam Muhajir1, Ace Tatang Hidayat1,3

  • 1Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Sumedang 45363, West Java, Indonesia.

Molecules (Basel, Switzerland)
|December 23, 2023
PubMed
Summary
This summary is machine-generated.

Epimerisation during peptide synthesis can alter peptide conformation and bioactivity. This review details factors inducing epimerisation, characterization methods, and strategies to suppress this critical side reaction.

Keywords:
cyclisationepimerisationpeptide synthesisside reactionsolid-phase peptide synthesis

More Related Videos

An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity
12:02

An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity

Published on: November 2, 2016

12.1K
Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library
13:37

Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library

Published on: June 20, 2014

18.2K

Related Experiment Videos

Last Updated: Jul 7, 2025

Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles PPAs and Related Biomaterials
08:55

Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles PPAs and Related Biomaterials

Published on: June 25, 2018

8.1K
An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity
12:02

An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity

Published on: November 2, 2016

12.1K
Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library
13:37

Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library

Published on: June 20, 2014

18.2K

Area of Science:

  • Organic Chemistry
  • Biochemistry
  • Peptide Synthesis

Background:

  • Epimerisation is a chemical transformation involving the conversion of an epimer to another epimer or its chiral partner.
  • Amino acid epimerisation is a common side reaction in peptide synthesis, often leading to undesirable changes in molecular conformation and bioactivity.
  • Epimerised products exhibit similar physical characteristics, complicating purification processes.

Purpose of the Study:

  • To review factors that induce epimerisation during peptide synthesis.
  • To discuss methods for characterising epimerised products and their impact on bioactivity.
  • To present strategies for suppressing undesirable epimerisation in peptide synthesis.

Main Methods:

  • Literature review of factors inducing epimerisation.
  • Discussion of analytical techniques for characterising epimerised amino acids and peptides.
  • Overview of established and novel methods for epimerisation suppression.

Main Results:

  • Identified key factors contributing to amino acid epimerisation during peptide synthesis.
  • Highlighted the challenges in purifying epimerised peptides due to similar physical properties.
  • Detailed the influence of epimerisation on peptide conformation and biological activity.

Conclusions:

  • Controlling epimerisation is crucial for maintaining peptide integrity and bioactivity.
  • Understanding the factors and mechanisms of epimerisation aids in developing effective suppression strategies.
  • This review provides a comprehensive guide to managing epimerisation in peptide synthesis.