Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Olefin Metathesis Polymerization: Overview

Olefin Metathesis Polymerization: Overview

Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...

Halogens

Halogens

Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group.

Stereoisomers

Stereoisomers

On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are stereoisomers that are not mirror images of each other. Substituted alkenes, such as the cis and trans isomers of 2-butene, are diastereomers, as these molecules exhibit different spatial orientations of their constituent atoms, are not mirror images of each other, and do not interconvert. Here, the interconversion is suppressed due to restricted...

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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...

Stereoisomerism of Cyclic Compounds

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...

You might also read

Related Articles

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

Sort by

Same author

Tube voltage-independent coronary calcium scoring on a first-generation dual-source photon-counting CT-a proof-of-principle phantom study.

The international journal of cardiovascular imaging·2021

Same author

Structured Digital Self-Assessment of Patient Anamnesis Prior to Computed Tomography: Performance Evaluation and Added Value.

Journal of medical systems·2021

Same author

Inhaled Pyrazinoic Acid Esters for the Treatment of Tuberculosis.

Pharmaceutical research·2016

Same author

A dry powder combination of pyrazinoic acid and its n-propyl ester for aerosol administration to animals.

International journal of pharmaceutics·2016

Same author

Novel iterative reconstruction method with optimal dose usage for partially redundant CT-acquisition.

Physics in medicine and biology·2015

Same author

Dose reduction in computed tomography of the chest: image quality of iterative reconstructions at a 50% radiation dose compared to filtered back projection at a 100% radiation dose.

RoFo : Fortschritte auf dem Gebiete der Rontgenstrahlen und der Nuklearmedizin·2014

Same journal

Erratum to: Immunotherapeutic Approach to Cancer with Cutaneous DNA Vaccination.

Methods in molecular medicine·2015

Same journal

Methods for cancer gene therapy using tumor suppressor genes.

Methods in molecular medicine·2014

Same journal

Suppression of the human carcinoma phenotype by an antioncogene ribozyme.

Methods in molecular medicine·2014

Same journal

Methods for the use of stromal cells for therapeutic gene therapy.

Methods in molecular medicine·2014

Same journal

Methods for adenovirus-mediated gene transfer to synovium in vivo.

Methods in molecular medicine·2014

Same journal

Methods for gene transfer to synovium.

Methods in molecular medicine·2014

See all related articles

Search research articles

Related Experiment Video

Updated: Jun 3, 2026

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

Fluoroolefin isosteres.

J T Welch¹, T Allmendinger

¹Department of Chemistry, State University of New York, Albany, New York.

Methods in Molecular Medicine

|March 8, 2011

Summary

This summary is machine-generated.

Unnatural peptides with modified backbones offer improved stability and activity. Researchers explored alkene and fluorinated alkene isosteres as amide bond replacements for enhanced peptide properties.

More Related Videos

Preparation of Hollow Polystyrene Particles and Microcapsules by Radical Polymerization of Janus Droplets Consisting of Hydrocarbon and Fluorocarbon Oils

Preparation of Hollow Polystyrene Particles and Microcapsules by Radical Polymerization of Janus Droplets Consisting of Hydrocarbon and Fluorocarbon Oils

Published on: January 25, 2018

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Related Experiment Videos

Last Updated: Jun 3, 2026

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

Preparation of Hollow Polystyrene Particles and Microcapsules by Radical Polymerization of Janus Droplets Consisting of Hydrocarbon and Fluorocarbon Oils

Preparation of Hollow Polystyrene Particles and Microcapsules by Radical Polymerization of Janus Droplets Consisting of Hydrocarbon and Fluorocarbon Oils

Published on: January 25, 2018

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Area of Science:

Medicinal Chemistry
Organic Chemistry
Biochemistry

Background:

The peptide backbone's amide bond is crucial for peptide structure and function.
Modifying the amide bond can enhance peptide activity, stability, and bioavailability.
Amide bond surrogates offer resistance to enzymatic degradation and conformational control.

Purpose of the Study:

To investigate the utility of alkene (ψ[C=C]) and fluorinated alkene (ψ[CF=C]) isosteres as replacements for the natural amide bond in peptides.
To evaluate how these isosteres mimic the steric and electronic properties of the amide bond.
To explore the potential of these unnatural peptide modifications for drug design.

Main Methods:

Synthesis and characterization of peptides incorporating ψ[C=C] and ψ[CF=C] isosteres.
Conformational analysis of the modified peptides.
Comparison of steric and electronic properties with natural amide bonds.

Main Results:

The ψ[C=C] isostere accurately mimics the steric properties of the amide bond and allows independent control of isomer formation.
The ψ[CF=C] isostere retains steric mimicry while accurately replicating the electronic features of the amide bond, including dipole moment and charge distribution.
Both isosteres offer conformational rigidity compared to the flexible natural amide bond.

Conclusions:

Alkene and fluorinated alkene isosteres are effective replacements for the amide bond in peptide design.
These modifications provide opportunities to fine-tune peptide conformation, stability, and electronic properties.
The ψ[CF=C] isostere is particularly promising for developing unnatural peptides with tailored characteristics.