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

Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

9.6K
Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
9.6K
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

9.4K
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
9.4K
Phase II Reactions: Acetylation Reactions01:24

Phase II Reactions: Acetylation Reactions

730
Acetylation, a phase II biotransformation reaction, introduces an acetyl group to drugs or their metabolites. Acetyltransferase enzymes facilitate this reaction, which resembles α-amino acid conjugation due to the addition of a functional group to the drug molecule.
The substrates for acetylation are typically drugs or their metabolites with an amino, sulfonamide, or hydrazine functional group. Acetylation can occur at several points in the drug molecule, including primary, secondary, and...
730
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones01:24

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

5.6K
Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
5.6K
Aldehydes and Ketones with Alcohols: Hemiacetal Formation01:19

Aldehydes and Ketones with Alcohols: Hemiacetal Formation

9.2K
Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
9.2K
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

4.0K
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
4.0K

You might also read

Related Articles

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

Sort by
Same author

Solid-Phase Glycolipid Synthesis Expedites Liposome Functionalization.

Journal of the American Chemical Society·2026
Same author

Topology Switching in Polymetallic Fragments Governed by Metal Encapsulation.

Journal of the American Chemical Society·2026
Same author

Plasmonic Nanocavity-Induced Degradation Pathway of Boronic Acid Biosensing Interfaces Revealed by <i>In Situ</i> Tip-Enhanced Raman Spectroscopy.

ACS nano·2026
Same author

Steroid Fingerprinting with Cryogenic Gas-Phase Infrared Spectroscopy.

ACS measurement science au·2026
Same author

Heparin-binding enhances extracellular listeriolysin O activity, overcoming cholesterol inhibition and pH dependence.

Journal of bacteriology·2026
Same author

Total synthesis of the capsular polysaccharide repeating unit towards the development of a glycoconjugate vaccine against <i>Klebsiella pneumoniae</i> ST512.

Beilstein journal of organic chemistry·2026

Related Experiment Video

Updated: Jan 7, 2026

Glycan Node Analysis: A Bottom-up Approach to Glycomics
11:36

Glycan Node Analysis: A Bottom-up Approach to Glycomics

Published on: May 22, 2016

11.1K

Evaluating Participation Modes in Peracetylated Glycosyl Cations.

Niklas Geue1,2, Kim Greis1,2, Sabrina Omoregbee-Leichnitz1,3

  • 1Institute of Chemistry and Biochemistry, Freie Universität Berlin, Altensteinstraße 23a, 14195 Berlin, Germany.

Organic Letters
|January 2, 2026
PubMed
Summary

Acetyl protecting groups in carbohydrate chemistry enable neighboring group participation, forming key dioxolenium ions in glucosyl, galactosyl, and mannosyl cations. Remote participation preferences vary by hexose, aiding future glycosylation strategies.

More Related Videos

Structural Characterization of Mannan Cell Wall Polysaccharides in Plants Using PACE
11:06

Structural Characterization of Mannan Cell Wall Polysaccharides in Plants Using PACE

Published on: October 16, 2017

10.1K
Profiling of Permethylated Mucin O-glycans Using Matrix-assisted Laser Desorption/Ionization Time-of-flight Mass Spectrometry
08:51

Profiling of Permethylated Mucin O-glycans Using Matrix-assisted Laser Desorption/Ionization Time-of-flight Mass Spectrometry

Published on: June 20, 2025

531

Related Experiment Videos

Last Updated: Jan 7, 2026

Glycan Node Analysis: A Bottom-up Approach to Glycomics
11:36

Glycan Node Analysis: A Bottom-up Approach to Glycomics

Published on: May 22, 2016

11.1K
Structural Characterization of Mannan Cell Wall Polysaccharides in Plants Using PACE
11:06

Structural Characterization of Mannan Cell Wall Polysaccharides in Plants Using PACE

Published on: October 16, 2017

10.1K
Profiling of Permethylated Mucin O-glycans Using Matrix-assisted Laser Desorption/Ionization Time-of-flight Mass Spectrometry
08:51

Profiling of Permethylated Mucin O-glycans Using Matrix-assisted Laser Desorption/Ionization Time-of-flight Mass Spectrometry

Published on: June 20, 2025

531

Area of Science:

  • Carbohydrate Chemistry
  • Organic Chemistry
  • Spectroscopy

Background:

  • Neighboring group participation and remote participation are crucial for stereocontrol in glycosylation reactions.
  • Glycosyl cations, key intermediates, are typically short-lived and difficult to characterize.
  • Acetyl protecting groups are commonly used in carbohydrate synthesis.

Purpose of the Study:

  • To directly assess and rank the participation modes of acetyl protecting groups in peracetylated glucosyl, galactosyl, and mannosyl cations.
  • To understand the influence of hexose structure on remote protecting group participation.
  • To provide fundamental insights into protecting group behavior in carbohydrate chemistry.

Main Methods:

  • Gas-phase infrared spectroscopy was employed to study glycosyl cations.
  • Density functional theory calculations were used to support experimental findings and rank theoretical structures.
  • Analysis focused on the formation of dioxolenium ions, indicative of participation.

Main Results:

  • Neighboring group participation, leading to C2-dioxolenium ion formation, was experimentally confirmed for all three hexoses (glucose, galactose, mannose).
  • Energetic analysis revealed distinct remote participation preferences: C3-dioxolenium ions for glucose and mannose, and C4-dioxolenium ions for galactose.
  • The stability of theoretical structures in vacuo differed based on the specific hexose.

Conclusions:

  • Acetyl protecting groups actively participate in glycosyl cation intermediates, influencing reaction stereochemistry.
  • The observed differences in remote participation highlight the importance of hexose structure in directing reaction pathways.
  • These findings enhance the fundamental understanding of protecting group dynamics and can inform the design of novel glycosylation strategies.