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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...
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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...
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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Stereoisomerism of Cyclic Compounds02:33

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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,...
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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.
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

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Related Experiment Video

Updated: May 20, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Peptide chirality sensing by a cyclodextrin-polythiophene conjugate.

Gaku Fukuhara1, Yoshihisa Inoue

  • 1Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita 565-0871, Japan. gaku@chem.eng.osaka-u.ac.jp

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 26, 2012
PubMed
Summary

A novel cyclodextrin-polythiophene conjugate (CDPT) was synthesized. While ineffective at inducing backbone chirality, CDPT successfully senses enantiomeric amino acids and dipeptides via UV/Vis spectral changes, with dipeptides showing higher selectivity.

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Published on: February 7, 2017

Area of Science:

  • Supramolecular Chemistry
  • Polymer Science
  • Analytical Chemistry

Background:

  • Polythiophene (PT) is a conducting polymer with potential applications in chiral sensing.
  • Cyclodextrins (CDs) are known for their ability to form inclusion complexes and induce chirality.
  • Conjugating CDs to PT could create novel materials for enantioselective recognition.

Purpose of the Study:

  • To synthesize a cyclodextrin-polythiophene conjugate (CDPT).
  • To investigate the CDPT's ability to induce homochiral structure in the polythiophene backbone.
  • To evaluate the CDPT's efficacy in sensing enantiomeric amino acids and dipeptides.

Main Methods:

  • Synthesis of permethyl-α-cyclodextrin conjugated to polythiophene via a hexamethylene tether.
  • Circular dichroism (CD) spectroscopy to assess induced chirality.
  • UV/Vis spectroscopy to monitor interactions with enantiomers.
  • Quantitative analysis of enantioselectivity.

Main Results:

  • CDPT exhibited weak Cotton effects in CD spectra, indicating limited induction of homochirality in the PT backbone.
  • CDPT showed chirality-dependent hypochromic changes in UV/Vis spectra upon addition of enantiomeric amino acids and dipeptides.
  • Dipeptide pairs, particularly Phe-Phe, were better differentiated than amino acid pairs, achieving a highest DD/LL selectivity of 13.7.

Conclusions:

  • Long tethers between cyclodextrins and polythiophene are ineffective for inducing backbone chirality.
  • CDPT serves as a sensitive chiral sensor for enantiomeric amino acids and dipeptides.
  • The developed CDPT system demonstrates potential for quantitative enantioselective sensing applications.