Related Experiment Video
Updated: Jul 18, 2026

07:26
Formation of Ordered Biomolecular Structures by the Self-assembly of Short Peptides
Published on: November 21, 2013
Parallel sheet structure in cyclopropane gamma-peptides stabilized by C-H...O hydrogen bonds
M Khurram N Qureshi1, Martin D Smith
1Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK.
Summary
A novel peptide structure was discovered. A three-residue trans-cyclopropane gamma-peptide forms infinite parallel sheets stabilized by hydrogen bonds, as shown by X-ray diffraction.
Area of Science:
- Peptide chemistry
- Supramolecular chemistry
- Crystallography
Background:
- Gamma-peptides are peptidomimetics with unique structural properties.
- Understanding peptide self-assembly is crucial for biomaterials and drug design.
Purpose of the Study:
- To investigate the solid-state structure of a three-residue trans-cyclopropane gamma-peptide.
- To elucidate the stabilizing interactions within the peptide assembly.
Main Methods:
- Single crystal X-ray diffraction was employed.
- Analysis of intermolecular interactions, specifically C-H...O hydrogen bonds.
Main Results:
- The gamma-peptide self-assembles into an infinite parallel sheet structure.
- Intermolecular C-H...O hydrogen bonds were identified as the primary stabilizing force.
- The trans-cyclopropane moiety influences the observed sheet conformation.
Conclusions:
- The study demonstrates a novel self-assembly pathway for gamma-peptides.
- The findings provide insights into the design of ordered peptide-based materials.
- This structural motif could be relevant for developing new molecular architectures.
More Related Videos
Related Concept Videos
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 tetrahedral value,...
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 tetrahedral value,...
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 staggered...
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...
Conformations of Cycloalkanes
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 was based on the...
Structures of Carboxylic Acid Derivatives
Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Protein Organization
Overview
Protein Organization
Proteins are polymers of amino acid residues. They are versatile and responsible for different cellular functions, including DNA replication, molecular transport, catalysis, and structural support. Proteins have a hierarchical structure comprising at least three levels of organization: primary, secondary, and tertiary structure. Some large proteins have a quaternary structure where individual protein subunits are linked together.
The primary structure of a protein is its amino acid sequence.
The primary structure of a protein is its amino acid sequence.

