Chemical Biology & Drug Design 2009-03-01

Methylation of alpha-amino acids and derivatives using trimethylsilyldiazomethane.

Antonella Leggio, Angelo Liguori, Francesca Perri, Carlo Siciliano, Maria Caterina Viscomi

Index: Chem. Biol. Drug Des. 73(3) , 287-91, (2009)

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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.