Di Gioia Maria Luisa, Leggio Antonella, Liguori Angelo, Perri Francesca
Dipartimento di Scienze Farmaceutiche, Università della Calabria, Via Ponte P. Bucci cubo 15/C, I-87036 Arcavacata di Rende (CS), Italy.
J Org Chem. 2007 May 11;72(10):3723-8. doi: 10.1021/jo070075m. Epub 2007 Apr 17.
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.
我们在此报告一种便捷且简单的固相合成方法，用于合成N-磺酰基-N-甲基-α-氨基酸和N-芴甲氧羰基-N-甲基-α-氨基酸，这些是合成构象受限和抗蛋白酶天然肽及肽类似物的重要组成部分。该方法包括使用2-氯三苯基氯树脂临时保护α-氨基酸的羧基，并使用重氮甲烷作为试剂对磺酰胺官能团进行甲基化。所开发的方法对于带有适当保护的官能化侧链的α-氨基酸也特别有效。
