Carrasco Michael R, Silva Oscar, Rawls Katherine A, Sweeney Marisol S, Lombardo Adria A
Department of Chemistry, Santa Clara University, Santa Clara, California 95053-0270, USA.
Org Lett. 2006 Aug 3;8(16):3529-32. doi: 10.1021/ol061289d.
Peptides containing N-alkylaminooxy amino acids were chemoselectively alkylated with allylic, benzylic, and alpha-carbonyl bromides, N-ethylmaleimide, and hexyl acrylate in mildly acidic aqueous/organic solutions. Alkylation at the aminooxy nitrogen proceeds in good yields with excellent to complete chemoselectivity in the presence of all common amino acids except cysteine. This reaction complements the selective glycosylation and acylation of N-alkylaminooxy groups and provides an avenue for the synthesis of peptide arrays comprising a wide variety of neoglycopeptides and neolipopeptides.
含有N-烷基氨氧基氨基酸的肽在弱酸性水/有机溶液中与烯丙基、苄基和α-羰基溴、N-乙基马来酰亚胺和丙烯酸己酯进行化学选择性烷基化反应。在除半胱氨酸外的所有常见氨基酸存在下，氨氧基氮上的烷基化反应产率良好，化学选择性优异至完全。该反应补充了N-烷基氨氧基的选择性糖基化和酰化反应，并为合成包含多种新糖肽和新脂肽的肽阵列提供了一条途径。
