Related Experiment Video
Updated: Jun 25, 2026

Exploring the Arginine Methylome by Nuclear Magnetic Resonance Spectroscopy
Published on: December 16, 2021
Methylation of alpha-amino acids and derivatives using trimethylsilyldiazomethane
Antonella Leggio1, Angelo Liguori, Francesca Perri
1Dipartimento di Scienze Farmaceutiche, Università della Calabria, Via P. Bucci, Cubo 15/C, I-87036 Arcavacata di Rende (CS), Italy.
Abstract:
A study of the methylation of N-nosyl-alpha-amino acids and derivatives with trimethylsilyldiazomethane is here reported. Trimethylsilyldiazomethane allows the chemo-specific methylation of the carboxyl function of N-nosyl-alpha-amino acids in high yields and purity. This method provides a practical route to N-methyl-alpha-amino acids avoiding the use of the more toxic and explosive diazomethane. This simple and safe methylation methodology of alpha-amino acids and derivatives is not limited to organic synthesis and involves the use of a commercially available reagent as well.
More Related Videos
Related Concept Videos
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Phase II Reactions: Methylation Reactions
The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...
Preparation and Reactions of Sulfides
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Diazonium Group Substitution: –OH and –H
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...

