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Related Concept Videos

Prochirality02:05

Prochirality

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...
Stereoisomerism of Cyclic Compounds02:33

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,...
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
Chirality in Nature02:30

Chirality in Nature

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. The...
Chirality02:25

Chirality

Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

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Related Experiment Video

Updated: May 30, 2026

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
09:22

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

Enhanced chiral recognition by cyclodextrin dimers.

Jens Voskuhl1, Kira Schaepe, Bart Jan Ravoo

  • 1Organic Chemistry Institute, Westfälische Wilhelms-Universität Münster, Correnstrasse 40, Münster 48149, Germany; E-Mails: jens.voskuhl@uni-muenster.de (J.V.); k_scha19@uni-muenster.de (K.S.).

International Journal of Molecular Sciences
|August 17, 2011
PubMed
Summary

Multivalency enhances chiral recognition. A cyclodextrin dimer showed increased enantioselectivity when binding to divalent chiral guests, demonstrating the power of multiple binding interactions.

Keywords:
chiral recognitioncyclodextrinshost-guest complexesisothermal titration calorimetrymultivalency

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

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Last Updated: May 30, 2026

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Engineering Molecular Recognition with Bio-mimetic Polymers on Single Walled Carbon Nanotubes
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Engineering Molecular Recognition with Bio-mimetic Polymers on Single Walled Carbon Nanotubes

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Area of Science:

  • Supramolecular Chemistry
  • Chiral Recognition
  • Host-Guest Chemistry

Background:

  • Chiral recognition is crucial in various scientific fields.
  • Understanding host-guest interactions is key to designing selective binding systems.
  • Multivalency can significantly influence binding affinity and selectivity.

Purpose of the Study:

  • To investigate the impact of multivalency on chiral recognition.
  • To synthesize and characterize carbohydrate-based divalent chiral guests.
  • To measure the binding interactions between a cyclodextrin dimer and divalent guests.

Main Methods:

  • Synthesis of water-soluble carbohydrate-based chiral guests.
  • Functionalization of guests with borneol, menthol, or isopinocampheol units.
  • Isothermal titration calorimetry (ITC) to determine host-guest interactions.

Main Results:

  • The cyclodextrin dimer binds to divalent guests with enhanced enantioselectivity.
  • Despite unfavorable conformations, multivalency leads to increased selectivity.
  • The study provides clear evidence for the effect of multivalency in chiral recognition.

Conclusions:

  • Multivalency is a key factor in achieving high enantioselectivity in host-guest systems.
  • Cyclodextrin dimers can be effective platforms for studying multivalency effects.
  • This research contributes to the understanding of molecular recognition and chiral discrimination.