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Stereoisomerism of Cyclic Compounds

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,...

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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.

Conformations of Cyclohexane

Conformations of Cyclohexane

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...

Chair Conformation of Cyclohexane

Chair Conformation of Cyclohexane

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...

Stability of Conjugated Dienes

Stability of Conjugated Dienes

Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.

Structure of Conjugated Dienes

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...

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Updated: Jun 25, 2025

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

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Published on: September 28, 2022

Comparison of Cyclic and Linear PEG Conjugates.

Grace E Kunkel¹, Qingyang Zhou¹, Joseph W Treacy¹

¹Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.

Bioconjugate Chemistry

|May 29, 2024

Summary

Cyclic polymer-protein bioconjugates offer improved stability and pharmacokinetics for biologic therapeutics. This study demonstrates the first conjugation of cyclic poly(ethylene glycol) (PEG) to T4 lysozyme, showing promising results for drug development.

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Area of Science:

Bioconjugation Chemistry
Polymer Science
Protein Engineering
Computational Biophysics

Background:

Polymer-protein bioconjugation enhances stability and pharmacokinetics of biologics.
The impact of polymer architecture, specifically cyclic structures, on bioconjugate properties remains largely unexplored.
Cyclic polymers exhibit unique characteristics, such as a smaller hydrodynamic radius compared to linear polymers of equivalent molecular weight.

Purpose of the Study:

To investigate the bioconjugation of a cyclic polymer, poly(ethylene glycol) (PEG), to a model protein, T4 lysozyme.
To compare the stability and activity of cyclic PEG-T4 lysozyme bioconjugates with linear PEG-T4 lysozyme analogues.
To explore the solution behavior of polymer-protein conjugates using molecular dynamics simulations.

Main Methods:

Engineered T4 lysozyme with a single cysteine residue (V131C) for site-specific bioconjugation.
Synthesized and characterized cyclic and linear poly(ethylene glycol) (PEG) for conjugation.
Performed bioconjugation reactions to create cyclic and linear PEG-T4 lysozyme conjugates.
Assessed conjugate stability and enzymatic activity.
Utilized molecular dynamics (MD) simulations to model conjugate behavior in solution.

Main Results:

Successfully achieved the first bioconjugation of a cyclic polymer (PEG) to T4 lysozyme.
Cyclic PEG-T4 lysozyme conjugates demonstrated comparable or improved stability and activity relative to linear PEG analogues.
MD simulations provided insights into the distinct solution dynamics influenced by polymer architecture.

Conclusions:

Cyclic polymer-protein conjugates represent a novel platform for enhancing biologic therapeutics.
The unique architecture of cyclic polymers can be leveraged to optimize bioconjugate properties.
This work lays the foundation for developing advanced cyclic polymer-based drug delivery systems.