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Updated: Jun 1, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
Published on: November 23, 2016
(S)-Benzyl 2-amino-3-(4-hydroxy-phen-yl)propanoate
Shu-Na Luo1, Lu Chen, Yu-Xing Gao
1Department of Chemistry and the Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China.
This study reveals the folded crystal structure of a novel compound, stabilized by hydrogen bonds. The synthesis likely retained the chiral integrity of the l-tyrosine starting material.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- Understanding molecular conformation and crystal packing is crucial in solid-state chemistry.
- Hydrogen bonding plays a significant role in stabilizing crystal lattices.
- Chiral integrity during synthesis is vital for producing enantiomerically pure compounds.
Purpose of the Study:
- To determine the crystal structure and conformation of the title compound C(16)H(17)NO(3).
- To investigate the intermolecular interactions stabilizing the crystal packing.
- To confirm the absolute configuration of the synthesized compound.
Main Methods:
- Single-crystal X-ray diffraction was employed to analyze the crystal structure.
- Analysis of bond lengths, angles, and intermolecular contacts.
- Assignment of absolute configuration based on the known stereochemistry of the starting material, l-tyrosine.
Main Results:
- The title compound C(16)H(17)NO(3) adopts a folded conformation in the solid state.
- Crystal packing is significantly stabilized by intermolecular hydrogen bonds (O-H⋯O and N-H⋯O).
- The absolute configuration was determined, assuming retention from l-tyrosine.
Conclusions:
- The synthesized compound exhibits a distinct folded conformation stabilized by hydrogen bonding.
- The synthetic route appears to preserve the stereochemical information from l-tyrosine.
- This structural information is valuable for understanding structure-property relationships in related molecules.
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