title: A versatile set of aminooxy amino acids for the synthesis of neoglycopeptides.
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 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.
authors: Department of Chemistry, Santa Clara University, Santa Clara, CA 95053-0270, USA. mcarrasco@scu.edu
authors: Michael R
authors: MR
authors: Carrasco
authors: Ryan T
authors: RT
authors: Brown
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D006020:Glycopeptides / Q000138:chemical synthesis*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000596:Amino Acids; D006020:Glycopeptides