Synthesis and NMR assignments of galactosylgloboside and its beta-D-GalNAc-(1-->4)-alpha-D-Gal-linked positional isomer in a conjugatable form.
Two pentasaccharides suitable for conjugation, namely 3-aminopropyl glactosylgloboside and its beta-D-GalNAc-(1-->4)-alpha-D-Gal-linked positional isomer, were synthesized from 3III,4III-di-O-unprotected globotrioside and the trichloroacetimidate of beta-D-Gal-(1-->3)-beta-D-GalNPhth derivative. Glycosylation at both positions led to the formation of beta-D-GalNPhth-(1-->4)-alpha-D-Gal and beta-D-GalNPhth-(1-->3)-alpha-D-Gal-linked products in a ratio of 1:1 without selectivity. Complete NMR spectral assignments are also described.
Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada. wei.zou@nrc.ca
W
W
Zou
J R
JR
Brisson
S
S
Larocque
R L
RL
Gardner
H J
HJ
Jennings
D015295:Antigens, Tumor-Associated, Carbohydrate; D002240:Carbohydrate Sequence; D006028:Glycosphingolipids / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D055746:Stage-Specific Embryonic Antigens
D015295:Antigens, Tumor-Associated, Carbohydrate; D006028:Glycosphingolipids; D055746:Stage-Specific Embryonic Antigens; C052924:stage-specific embryonic antigen-3