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Phase II Reactions: Acetylation Reactions01:24

Phase II Reactions: Acetylation Reactions

Acetylation, a phase II biotransformation reaction, introduces an acetyl group to drugs or their metabolites. Acetyltransferase enzymes facilitate this reaction, which resembles α-amino acid conjugation due to the addition of a functional group to the drug molecule.
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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
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A Strategy for Sensitive, Large Scale Quantitative Metabolomics
14:18

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Published on: May 27, 2014

N-Acryloylphenyl-alanine.

Cong-Ren Wu, Xiao-Feng Gao, Hai-Bo Wang

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary
    This summary is machine-generated.

    Researchers synthesized a novel compound, C(12)H(13)NO(3), using acryloyl chloride and glycylglycine. The crystal structure reveals extensive intermolecular hydrogen bonding forming a 3D network.

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    Published on: November 23, 2016

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Supramolecular Chemistry

    Background:

    • Glycylglycine is a dipeptide with reactive amine and carboxylic acid groups.
    • Acryloyl chloride is a reactive acyl chloride used in organic synthesis.
    • Hydrogen bonding plays a crucial role in molecular self-assembly and crystal engineering.

    Purpose of the Study:

    • To synthesize and characterize a novel compound derived from glycylglycine and acryloyl chloride.
    • To investigate the crystal structure and intermolecular interactions of the synthesized compound.
    • To understand the role of hydrogen bonding in the formation of a three-dimensional network.

    Main Methods:

    • Nucleophilic substitution reaction between acryloyl chloride and glycylglycine.
    • Single-crystal X-ray diffraction analysis to determine the crystal structure.
    • Analysis of intermolecular interactions, including hydrogen bonds (N-H⋯O, O-H⋯O, C-H⋯O).

    Main Results:

    • Successful synthesis of the title compound, C(12)H(13)NO(3).
    • The crystal structure exhibits a robust three-dimensional network.
    • Multiple types of intermolecular hydrogen bonds (N-H⋯O, O-H⋯O, C-H⋯O) are identified as the primary driving force for network formation.

    Conclusions:

    • The reaction of acryloyl chloride with glycylglycine yields a compound with a defined crystal structure.
    • Intermolecular hydrogen bonding is essential for the assembly of molecules into a stable 3D network.
    • This study contributes to the understanding of crystal engineering and supramolecular assembly through hydrogen bond interactions.