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Related Concept Videos

Prochirality02:05

Prochirality

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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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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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Chirality02:25

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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.
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...
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Molecules with Multiple Chiral Centers02:25

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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...
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Chirality in Nature02:30

Chirality in Nature

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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.
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Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

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The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Axially Chiral Cannabinoids: Design, Synthesis, and Cannabinoid Receptor Affinity.

Sara E Kearney1, Anghelo J Gangano1, Daniel G Barrus2

  • 1Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.

Journal of the American Chemical Society
|June 14, 2023
PubMed
Summary
This summary is machine-generated.

Researchers developed novel axially chiral cannabinols (axCBNs) and cannabidiols (axCBDs) by modifying the cannabinoid structure. These new compounds show promise for enhanced therapeutic properties and drug development targeting the endocannabinoid system.

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Pharmacology

Background:

  • The resorcinol-terpene scaffold is key for developing therapeutics targeting the endocannabinoid system.
  • Axially chiral cannabinols (axCBNs) are unnatural analogs with enhanced physical and biological properties.
  • Axially chiral cannabidiols (axCBDs) are a new class inspired by cannabidiol (CBD).

Purpose of the Study:

  • To explore the design philosophy and synthetic strategies for axially chiral cannabinoids (axCBNs and axCBDs).
  • To analyze the atropisomerism of axCannabinoids.
  • To evaluate the affinity and functional activity of axCannabinoids at cannabinoid receptors.

Main Methods:

  • Design and synthesis of axially chiral cannabinols (axCBNs) and cannabidiols (axCBDs).
  • Analysis of atropisomerism in axCannabinoids.
  • Assessment of receptor binding affinity and functional activity at cannabinoid receptors.

Main Results:

  • Successful synthesis of novel axCBNs and axCBDs.
  • Characterization of axCannabinoid atropisomerism (class 1 and 3).
  • Demonstrated retention and, in some cases, strengthening of affinity and activity at cannabinoid receptors.

Conclusions:

  • Axially chiral cannabinoids represent a promising new direction for designing novel cannabinoid ligands.
  • These compounds offer potential for drug discovery and exploring the endocannabinoid system.
  • The unique structural modifications enhance ligand properties for therapeutic applications.