A new strategy for stereoselective synthesis of sialic acid-containing glycopeptide fragment.
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.
Wang
Z G
ZG
Institute of Physical and Chemical Research (RIKEN), Saitama, Japan.
Zhang
X F
XF
Ito
Y
Y
Nakahara
Y
Y
Ogawa
T
T
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
D006020:Glycopeptides; D010446:Peptide Fragments; D019158:N-Acetylneuraminic Acid