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Related Concept Videos

Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

14.3K
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.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
14.3K
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

807
At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
807
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

12.1K
Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
12.1K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.8K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
2.8K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.7K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
2.7K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

11.5K
Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
11.5K

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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Cyclic Peptide C5aR1 Antagonist Design Using Solution Conformational Analysis Derived from Residual Dipolar

Kathleen A Farley1, Ye Che1, Ricardo Lira1

  • 1Medicine Design, Pfizer Inc., 445 Eastern Point Rd, Groton, Connecticut 06340, United States.

ACS Medicinal Chemistry Letters
|November 20, 2024
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Summary

Researchers uncovered three distinct solution conformations for cyclic peptides targeting the C5a receptor (C5aR1). This conformational data guides the design of more potent peptide therapeutics by mimicking the target-bound state.

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Construction of Cyclic Cell-Penetrating Peptides for Enhanced Penetration of Biological Barriers
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Area of Science:

  • Medicinal Chemistry
  • Structural Biology
  • Pharmacology

Background:

  • G-protein coupled receptors (GPCRs) are crucial drug targets.
  • Small cyclic peptides are emerging as potent modulators of GPCRs.
  • Understanding peptide conformation is key to optimizing drug design.

Purpose of the Study:

  • To elucidate the solution conformations of cyclic peptides binding to the C5a receptor 1 (C5aR1).
  • To utilize these conformations for designing more potent peptide-based therapeutics.
  • To establish a framework for structure-based peptide drug design.

Main Methods:

  • Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Residual dipolar couplings (RDCs) for structural determination.
  • NMR temperature coefficients to identify hydrogen bonding patterns.

Main Results:

  • Three unique solution conformations were determined for distinct cyclic peptides.
  • Each peptide exhibited a different intramolecular hydrogen bonding pattern.
  • Conformational insights were applied to design more potent C5aR1-targeting peptides.

Conclusions:

  • Solution conformations of cyclic peptides can be accurately determined using RDCs and NMR temperature coefficients.
  • This approach provides a valuable framework for structure-guided design of peptide mimetics.
  • Minimizing bound state strain energy through conformational design enhances peptide potency.