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Embryo Rescue Protocol for Interspecific Hybridization in Squash
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Published on: September 12, 2022

Cucurbit[n]urils: from mechanism to structure and function.

Lyle Isaacs1

  • 1Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA. lisaacs@umd.edu

Chemical Communications (Cambridge, England)
|March 27, 2009
PubMed
Summary
This summary is machine-generated.

Cucurbit[n]urils (CB[n]) are molecular containers with unique recognition abilities. Partially formed CB[n] intermediates, nor-seco-CB[n], exhibit chiral recognition and allostery, acting as aldehyde synthons.

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Published on: December 5, 2019

Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Cucurbit[n]urils (CB[n]) are macrocyclic hosts known for their strong molecular recognition capabilities.
  • The synthesis of CB[n] involves the condensation of glycoluril with formaldehyde.
  • Understanding the formation pathway and intermediate structures is crucial for designing novel host molecules.

Purpose of the Study:

  • To detail the unusual recognition properties of the cucurbit[n]uril (CB[n]) family.
  • To elucidate the mechanism of CB[n] formation, including key intermediates.
  • To describe the structure and function of nor-seco-CB[n] intermediates.

Main Methods:

  • Review of literature on cucurbit[n]uril synthesis and properties.
  • Analysis of structural data for CB[n] and related macrocyclic intermediates.
  • Discussion of experimental evidence for the recognition properties of nor-seco-CB[n].

Main Results:

  • Cucurbit[n]uril formation proceeds through methylene-bridged glycoluril oligomers.
  • Kinetically stable macrocyclic intermediates, nor-seco-CB[n], were identified.
  • Nor-seco-CB[n] exhibit chiral recognition, homotropic allostery, and act as aldehyde reaction synthons.

Conclusions:

  • Partially formed cucurbit[n]uril structures (nor-seco-CB[n]) possess unique and valuable recognition properties.
  • These intermediates offer new avenues for designing tailored molecular receptors.
  • Nor-seco-CB[n] expand the utility of cucurbiturils in host-guest chemistry and synthesis.