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Updated: Jun 1, 2026
09:57
A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles
Published on: December 23, 2016
(RSS)-[N-Hydroxyethyloxy]-hexafluoroVal-MeLeu-Ala tert-butyl ester
Summary
This study details the crystal structure of a novel tripeptide, revealing its chiral ortho-rhom-bic spacegroup and specific stereochemistry. Intramolecular hydrogen bonds stabilize its coiled conformation with external hydrophobic groups.
Area of Science:
- Crystallography
- Organic Chemistry
- Structural Biology
Background:
- Tripeptides are fundamental building blocks in biological systems.
- Understanding the solid-state structure of modified peptides is crucial for drug design.
- Fluorinated amino acids offer unique properties for peptide modification.
Purpose of the Study:
- To determine the crystal structure and absolute configuration of a novel fluorinated tripeptide.
- To investigate the solid-state conformation and intermolecular interactions.
- To characterize the positional disorder of a key substituent.
Main Methods:
- Single-crystal X-ray diffraction analysis.
- Absolute configuration determination based on known stereochemistry.
- Analysis of intra-molecular hydrogen bonding and structural features.
Main Results:
- The title compound crystallizes in the chiral ortho-rhom-bic spacegroup P2(1)2(1)2(1).
- The absolute configuration (R) of the hexa-fluoro-valine unit was established.
- Positional disorder was observed in the N-hydroxy-ethyl-oxy substituent.
- Intra-molecular N-H⋯F and N-H⋯O hydrogen bonds stabilize a coiled structure.
Conclusions:
- The study provides a detailed structural characterization of a unique fluorinated tripeptide.
- The findings highlight the role of hydrogen bonding in stabilizing peptide conformations.
- The observed disorder offers insights into molecular flexibility in the solid state.
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