The Journal of organic chemistry

A versatile set of aminooxy amino acids for the synthesis of neoglycopeptides

MR Carrasco, RT Brown

Index: Carrasco, Michael R.; Brown, Ryan T. Journal of Organic Chemistry, 2003 , vol. 68, # 23 p. 8853 - 8858

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Citation Number: 85

Abstract

Four N-alkylaminooxy amino acids have been synthesized in 22-56% overall yield from readily available amino acid precursors. Each amino acid can be efficiently incorporated into peptides using Boc-chemistry-based solid-phase peptide synthesis, and in three of the four cases the resulting peptides can be chemoselectively glycosylated at the aminooxy side chains to generate neoglycopeptides. The range of N-alkylaminooxy amino acids ...