Solid-phase synthesis of N-nosyl- and N-Fmoc-N-methyl-alpha-amino acids.
We report here a convenient and simple solid-phase synthesis of N-nosyl-N-methyl-alpha-amino acids and N-Fmoc-N-methyl-alpha-amino acids, important building blocks for the synthesis of conformationally restricted and protease-resistant natural peptides and peptide analogues. The methodology involves the use of 2-chlorotrityl chloride resin to temporarily protect the carboxylic group of alpha-amino acids and of diazomethane as the reagent to methylate the sulfonamidic function. The approach developed is particularly efficient also with alpha-amino acids bearing appropriately protected functionalized side chains.
Di Gioia
Maria Luisa
ML
Dipartimento di Scienze Farmaceutiche, Università della Calabria, Via Ponte P. Bucci cubo 15/C, I-87036 Arcavacata di Rende (CS), Italy.
Leggio
Antonella
A
Liguori
Angelo
A
Perri
Francesca
F
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D005449:Fluorenes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D015394:Molecular Structure
D000596:Amino Acids; D005449:Fluorenes