jo034984x_si_001.pdf (6.45 MB)
A Versatile Set of Aminooxy Amino Acids for the Synthesis of Neoglycopeptides
journal contribution
posted on 2003-10-14, 00:00 authored by Michael R. Carrasco, Ryan T. BrownFour 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 prepared allows attachment of sugars at two-,
three-, or four-atom distances from the peptide backbone, and each ensures that attached sugars
adopt cyclic conformations. These derivatives provide convenient access to arrays of biologically
relevant neoglycopeptides that may be used to probe the influence of attached sugars on the
structure and function of peptides and proteins.