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

Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

10.6K
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,...
10.6K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

14.1K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
14.1K
Protecting Groups for Aldehydes and Ketones: Introduction01:23

Protecting Groups for Aldehydes and Ketones: Introduction

8.3K
Protecting groups are compounds that can bind to a specific functional group in the presence of other functional groups to protect them from undesired chemical reactions. These compounds can selectively bind to particular functional groups and advance chemoselective reactions in polyfunctional systems (Figure 1). After the functional group has served its purpose, it is removed by reacting it with specific compounds.
8.3K
Prochirality02:05

Prochirality

4.6K
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
4.6K
Chirality in Nature02:30

Chirality in Nature

15.6K
Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.
15.6K
Cycloalkanes02:28

Cycloalkanes

14.7K
Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
14.7K

You might also read

Related Articles

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

Sort by
Same author

Zn(II) complexation promotes isomerization and oxidative rearrangements of naringenin: evidence from IR ion spectroscopy and DFT calculations.

Dalton transactions (Cambridge, England : 2003)·2026
Same author

Acetaldehyde as CH<sub>2</sub> <sup>+•</sup> Acceptor: Characterization of an Ionic Adduct Possibly Playing a Role in the Astronomical Environment.

ACS physical chemistry Au·2026
Same author

Genitourinary Microbiome and Volatilome: A Pilot Study in Patients with Prostatic Adenocarcinoma Submitted to Radical Prostatectomy.

Cancers·2025
Same author

Identification of D-Fructose Dehydration Products by Infrared Multiphoton Dissociation Mass Spectrometry: The Spectral Signature of An Elusive 5-Hydroxymethylfurfural Isomer.

ChemistryOpen·2025
Same author

Comparative Profiling of Volatile Compounds and Fatty Acids in Pomegranate Seed Oil: Soxhlet vs. CO<sub>2</sub>/IPA Extraction for Quality and Circular Bioeconomy Goals.

Foods (Basel, Switzerland)·2025
Same author

Enhancing Human Health Through Nutrient and Bioactive Compound Recovery from Agri-Food By-Products: A Decade of Progress.

Nutrients·2025

Related Experiment Video

Updated: Nov 19, 2025

Author Spotlight: Unveiling the Structural and Dynamic Aspects of Glycan Molecular Recognition
07:40

Author Spotlight: Unveiling the Structural and Dynamic Aspects of Glycan Molecular Recognition

Published on: May 17, 2024

1.7K

Unprotected Galactosamine as a Dynamic Key for a Cyclochiral Lock.

Caterina Fraschetti1, Matthias C Letzel2, Marlene Paletta3

  • 1Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza-Università di Roma, Piazzale Aldo Moro 5, I-00185 Rome, Italy.

Journal of the American Society for Mass Spectrometry
|January 27, 2021
PubMed
Summary

This study used mass spectrometry to differentiate amino sugars like d-galactosamine (G) using chiral resorcin[4]arenes (C). The complexes showed varied reactivity with amines, influenced by cyclochirality and formation environment.

More Related Videos

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
08:46

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

9.0K
Cycloheximide Chase Analysis of Protein Degradation in Saccharomyces cerevisiae
09:05

Cycloheximide Chase Analysis of Protein Degradation in Saccharomyces cerevisiae

Published on: April 18, 2016

29.5K

Related Experiment Videos

Last Updated: Nov 19, 2025

Author Spotlight: Unveiling the Structural and Dynamic Aspects of Glycan Molecular Recognition
07:40

Author Spotlight: Unveiling the Structural and Dynamic Aspects of Glycan Molecular Recognition

Published on: May 17, 2024

1.7K
Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
08:46

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

9.0K
Cycloheximide Chase Analysis of Protein Degradation in Saccharomyces cerevisiae
09:05

Cycloheximide Chase Analysis of Protein Degradation in Saccharomyces cerevisiae

Published on: April 18, 2016

29.5K

Area of Science:

  • Supramolecular Chemistry
  • Analytical Chemistry
  • Mass Spectrometry

Background:

  • Amino sugars, like d-galactosamine (G), are crucial in biological systems.
  • Discriminating chiral molecules requires sophisticated analytical techniques.
  • Supramolecular complexes can be designed for selective guest binding and reactivity modulation.

Purpose of the Study:

  • To investigate the discrimination of d-galactosamine (G) using enantiomers of cyclochiral resorcin[4]arenes (C).
  • To probe the reactivity of [C·H·G]+ proton-bound complexes with primary amines (B).
  • To understand how supramolecular architecture and cyclochirality influence guest-host interactions and reactivity.

Main Methods:

  • Nano-ESI-FT-ICR mass spectrometry was employed to generate and analyze proton-bound complexes.
  • Complexes of d-galactosamine (G) with resorcin[4]arene enantiomers (C) were formed.
  • Reactions of these complexes with various primary amines (B) were studied to observe ligand exchange and isomerization.

Main Results:

  • Three types of [C·H·G]+ aggregates were identified ([C·H·G]+ESI, [C·H·G]+GAS, [C·H·G]+SOL), exhibiting distinct origins and reactivities.
  • Electrospray-generated adducts ([C·H·G]+ESI) underwent ligand exchange with amines and partial isomerization.
  • A cyclochirality effect on reactivity was observed, dependent on the specific aggregate type.

Conclusions:

  • The study successfully demonstrated the discrimination of d-galactosamine using chiral resorcin[4]arene hosts.
  • The reactivity of the supramolecular complexes is tunable by the basicity of the amine guest and influenced by the complex's formation environment.
  • Cyclochirality plays a significant role in modulating the reactivity of these host-guest systems.