Related Experiment Video
Updated: May 25, 2025
10:39
Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
Published on: August 23, 2018
7.8K
Actions and Interactions of Mirror-Image Cyclodextrins
Daniel W Armstrong1,2, Saba Aslani1,2, Jordan Nafie3
1University of Texas at Arlington, Arlington, Texas 76019, United States.
JACS Au
|February 28, 2025
Summary
Researchers successfully separated mirror-image cyclodextrins (CDs) using vibrational circular dichroism (VCD). This breakthrough enables selective excitation and diverse applications for these chiral molecules in medicine and biochemistry.
Area of Science:
- Macrocyclic science and technology
- Carbohydrate chemistry
- Stereochemistry
Background:
- Cyclodextrins (CDs) are pivotal macrocyclic molecules with inherent chirality.
- Their inclusion complexation properties are well-established.
- The recent synthesis of unnatural l-cyclodextrins opens new avenues in stereochemical research.
Purpose of the Study:
- To achieve rapid and sensitive separation of enantiomeric cyclodextrins.
- To investigate and distinguish the absolute configurations of CD antipodes.
- To explore the potential applications of enantiomeric CDs.
Main Methods:
- Separation of enantiomeric cyclodextrins.
- Vibrational circular dichroism (VCD) spectroscopy for configuration analysis.
- Electrophoretic migration studies of chiral molecules.
Main Results:
- Successfully separated enantiomeric cyclodextrins.
- Identified a key VCD band at 1150 cm-1 related to glucosidic bond C-O stretching, distinguishing d- and l-CDs.
- Demonstrated selective excitation of CD enantiomers by chiroptical radiation.
- Observed significant differences in enzymatic susceptibility between mirror-image CDs.
- Showcased predictable reversal of electrophoretic migration for chiral molecules using d- and l-CDs.
Conclusions:
- Enantiomeric cyclodextrins can be effectively separated and distinguished using VCD.
- Chiroptical radiation offers selective excitation of CD enantiomers.
- Mirror-image CDs exhibit distinct biochemical properties, suggesting varied medicinal and biochemical applications.
- Enantiomeric CDs can modulate the electrophoretic behavior of chiral molecules.
Related Concept Videos
02:33Stereoisomerism of Cyclic Compounds
8.7K
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,...
8.7K
02:32Stereoisomers
12.4K
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...
12.4K
02:52Stereoisomerism
11.7K
Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
11.7K
02:24Properties of Enantiomers and Optical Activity
16.6K
It is essential to understand the difference between chiral and achiral interactions and the implications thereof in optical activity and their applications. Just as our feet, which are chiral, interact uniquely with chiral objects, such as a pair of shoes, but identically with achiral socks, enantiomers of a molecule exhibit different properties only when they interact with other chiral media. An example of a significant implication from this facet is the phenomenon known as optical activity,...
16.6K
02:37Disubstituted Cyclohexanes: cis-trans Isomerism
11.7K
Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
11.7K
01:16Cycloaddition Reactions: MO Requirements for Thermal Activation
3.5K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
3.5K