title: A new strategy for stereoselective synthesis of sialic acid-containing glycopeptide fragment.
abstract: Sialic acid donor 5, which has a thiophenyl group as a stereocontrolling auxiliary and thiomethyl group as a leaving group was prepared and subjected to model glycosylation. Reactions with acceptor substrates 6, 7, and 8 gave coupled products 9b, 10b, and 11b, respectively, in a higher efficiency than previously observed for the bromide 1a. This reaction was further applied to the synthesis of protected glyco-amino acid fragment 12, that is strategically designed for the synthesis of sialic acid containing glycopeptides.
authors.affiliation: Institute of Physical and Chemical Research (RIKEN), Saitama, Japan.
authors.forename: Z G
authors.initials: ZG
authors.lastname: Wang
authors.forename: X F
authors.initials: XF
authors.lastname: Zhang
authors.forename: Y
authors.initials: Y
authors.lastname: Ito
authors.forename: Y
authors.initials: Y
authors.lastname: Nakahara
authors.forename: T
authors.initials: T
authors.lastname: Ogawa
mesh_terms: D002240:Carbohydrate Sequence; D006020:Glycopeptides / Q000737:chemistry*; D008969:Molecular Sequence Data; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*; D010446:Peptide Fragments / Q000138:chemical synthesis*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism
chemical_list: D006020:Glycopeptides; D010446:Peptide Fragments; D019158:N-Acetylneuraminic Acid