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

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...

You might also read

Related Articles

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

Sort by
Same author

A Bifunctional Aminoxyl-Bipyridine Peptide Catalyst for the Atroposelective Copper-Catalyzed Aerobic Oxidation of Biaryl Diols.

Journal of the American Chemical Society·2026
Same author

Assessment of Complementary Catalysts in an Uncharted Enantioselective Reaction of Sulfondiimines.

Journal of the American Chemical Society·2026
Same author

Site-Divergent Oxidations within Venerable Macrolide Antibiotic Scaffolds Unveil Compounds with Broad Spectrum and Anti-MRSA Activities.

ACS central science·2026
Same author

Asymmetric Hydrogen Atom Transfer.

ACS catalysis·2026
Same author

Asymmetric Desymmetrizing Sulfonylation of Diarylmethanes via Peptidyl-Cu(I)-Catalysis with Remote Stereocontrol.

Journal of the American Chemical Society·2026
Same author

Peptide-Catalyzed Asymmetric Amination of Sulfenamides Enabled by DFT-Guided Catalyst Optimization.

Journal of the American Chemical Society·2025

Related Experiment Video

Updated: May 23, 2026

Nanomechanics of Drug-target Interactions and Antibacterial Resistance Detection
11:56

Nanomechanics of Drug-target Interactions and Antibacterial Resistance Detection

Published on: October 25, 2013

Site-selective bromination of vancomycin.

Tejas P Pathak1, Scott J Miller

  • 1Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, USA.

Journal of the American Chemical Society
|April 3, 2012
PubMed
Summary
This summary is machine-generated.

Researchers achieved site-selective bromination of vancomycin, creating novel monobromovancomycins. A peptide promoter enhanced reaction rates and altered product distribution for vancomycin modification.

More Related Videos

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
12:31

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Related Experiment Videos

Last Updated: May 23, 2026

Nanomechanics of Drug-target Interactions and Antibacterial Resistance Detection
11:56

Nanomechanics of Drug-target Interactions and Antibacterial Resistance Detection

Published on: October 25, 2013

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
12:31

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Biochemistry

Background:

  • Vancomycin is a critical antibiotic for treating serious Gram-positive bacterial infections.
  • Modifying vancomycin can overcome emerging resistance mechanisms.
  • Site-selective functionalization of complex molecules like vancomycin remains challenging.

Purpose of the Study:

  • To develop a method for site-selective bromination of vancomycin.
  • To investigate the influence of promoters on vancomycin bromination.
  • To explore alternative conditions for controlling vancomycin functionalization.

Main Methods:

  • Direct bromination of vancomycin using N-bromophthalimide.
  • Utilizing a rationally designed peptide-based promoter to influence reactivity.
  • Investigating the effect of solvent and guanidine as replacements for the peptide promoter.

Main Results:

  • Substantial efficiency in producing novel monobromovancomycins, a dibromovancomycin, and a tribromovancomycin.
  • Demonstrated significant rate acceleration of vancomycin bromination with the peptide promoter.
  • Observed altered product distribution and alternative site selectivity influenced by the promoter, solvent, and guanidine.

Conclusions:

  • Site-selective bromination of vancomycin is achievable with high efficiency.
  • Peptide-based promoters can significantly enhance and control vancomycin functionalization.
  • Solvent and alternative additives like guanidine offer further tunability for vancomycin modification.