Enzymatic synthesis of Kdn oligosaccharides by a bacterial alpha-(2-->6)-sialyltransferase.
Synthesis of CMP-deaminoneuraminic acid (CMP-beta-D-Kdn) and its enzymatic transfer reaction using bacterial alpha-(2-->6)-sialyltransferase were examined. CMP-beta-D-Kdn was prepared from methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-beta-D-galacto-2- nonulopyranosonate (2) in 24% overall yield. Enzymatic synthesis of Kdn oligosaccharide with CMP-beta-D-Kdn (10.2 mumol), methyl beta-D-lactosaminide (7, 8.1 mumol) and purified sialyltransferase (80 munits) afforded Kdn-alpha-(2-->6)-Gal-beta-(1-->4)-GlcNAc-beta-1-OMe in 77% yield.
Kajihara
Y
Y
Department of System Function, Faculty of Science, Yokohama City University, Japan. kajihara@yokohama-cu.ac.jp
Akai
S
S
Nakagawa
T
T
Sato
R
R
Ebata
T
T
Kodama
H
H
Sato
K
K
D000606:Amino Sugars / Q000737:chemistry; D002240:Carbohydrate Sequence; D003568:Cytidine Monophosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006027:Glycosides / Q000737:chemistry; D006923:Hymecromone / Q000031:analogs & derivatives / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009438:Neuraminic Acids / Q000138:chemical synthesis*; D012799:Sialyltransferases / Q000737:chemistry*
C102546:4-methylumbelliferyl lactoside; D000606:Amino Sugars; D006027:Glycosides; D009438:Neuraminic Acids; C120601:methyl-acetyl-lactosaminide; C079495:CMP-deaminoneuraminic acid; D006923:Hymecromone; D012799:Sialyltransferases; D003568:Cytidine Monophosphate