A chemical synthesis of UDP-LacNAc and its regioisomer for finding 'oligosaccharide transferases'.
A chemical synthesis of uridine 5'-diphospho-N-acetyllactosamine (Galbeta(1-->4)GlcNAc-UDP; UDP-LacNAc) and Galbeta(1-->3)GlcNAc-UDP is described. Coupling of the disaccharide imidate derivatives with dibenzylphosphate gave the corresponding 1-phosphates, which were condensed with UMP-imidazolate to give the target UDP-oligosaccharides after purification by anion exchange HPLC and gel filtration column chromatography. Using this methodology a variety of oligosaccharide nucleotide analogues can be synthesized. These UDP-oligosaccharides may be useful for finding so-called ;oligosaccharide transferases', the glycosyltransferases which transfer the oligosaccharide moiety onto glycosyl acceptors.
Takaku
Hironao
H
United Graduate School of Agricultual Science, Gifu University, Yanagido, Gifu, 501-1193, Japan.
Sato
Junhei
J
Ishida
Hide-Ki
HK
Inazu
Toshiyuki
T
Ishida
Hideharu
H
Kiso
Makoto
M
D006602:Hexosyltransferases / Q000378:metabolism*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008565:Membrane Proteins / Q000378:metabolism*; D015394:Molecular Structure; D013237:Stereoisomerism; D013379:Substrate Specificity; D014539:Uridine Diphosphate Sugars / Q000138:chemical synthesis* / Q000737:chemistry
D008565:Membrane Proteins; D014539:Uridine Diphosphate Sugars; C083732:uridine diphosphate N-acetyllactosamine; D006602:Hexosyltransferases; C025620:dolichyl-diphosphooligosaccharide - protein glycotransferase