Related Experiment Video
Updated: Oct 18, 2025

A Facile Protocol to Generate Site-Specifically Acetylated Proteins in Escherichia Coli
Published on: December 9, 2017
Site-Selective Molecular Transformation: Acylation of Hydroxy Groups and C-H Amination
1Institute for Chemical Research, Kyoto University.
Abstract:
Control of site selectivity is an exciting direction for synthetic organic chemistry owing to the possibility of selective modification of multifunctionalized molecules, ultimately including biomacromolecules. In this review, our recent research related to site selectivity in two types of transformation, namely, the acylation of hydroxy groups and C-H amination, is summarized. Regarding the acylation of hydroxy groups, catalyst-controlled site selectivity enables unconventional retrosynthetic analysis, leading to efficient syntheses of sugar-related natural and unnatural products. Regarding C-H amination, the discovery of unprecedented reaction sites in intermolecular amination mediated by dirhodium nitrenes is described. The findings of this research demonstrate the power of site-selective transformation in the synthesis of a particular class of compounds.
Related Concept Videos
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Phase II Reactions: Acetylation Reactions
The substrates for acetylation are typically drugs or their metabolites with an amino, sulfonamide, or hydrazine functional group. Acetylation can occur at several points in the drug molecule, including primary, secondary, and...
Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

