Effective chemoenzymatic synthesis of p-aminophenyl glycosides of sialyl N-acetyllactosaminide and analysis of their interactions with lectins.
A convenient chemoenzymatic procedure for the synthesis of p-aminophenyl glycosides of sialyl N-acetyllactosaminide has been developed from p-nitrophenyl N-acetyl-beta-D-glucosaminide as starting material through three steps: synthesis of p-nitrophenyl N-acetyllactosaminide with beta-D-galactosidase, chemical reduction of the p-nitrophenyl group, and sialylation with sialyltransferase. The p-aminophenyl glycosides were then successfully biotin-labeled through the coupling with N-(+)-biotinyl-6-aminohexanoic acid to afford biotinylated oligosaccharides with an aminohexanosyl group and phenyl group as the spacers between the biotin and glycan. Furthermore, the biotin-labeled sugars were shown to be useful for immobilization and assay of the carbohydrate-lectin interactions by an optical biosensor based on surface plasmon resonance.
Zeng
Xiaoxiong
X
Department of Biotechnology, College of Food Science and Technology, Nanjing Agricultural University, Weigang, Nanjing 210095, Jiangsu, PR China. zengxx@njau.edu.cn
Sun
Yi
Y
Ye
Hong
H
Liu
Jun
J
Xiang
Xiaoli
X
Zhou
Bei
B
Uzawa
Hirotaka
H
D000606:Amino Sugars / Q000737:chemistry*; D001710:Biotin / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D037102:Lectins / Q000737:chemistry*; D007930:Leucine / Q000031:analogs & derivatives; D008969:Molecular Sequence Data; D015394:Molecular Structure; D012799:Sialyltransferases / Q000737:chemistry / Q000378:metabolism; D020349:Surface Plasmon Resonance; D001616:beta-Galactosidase / Q000737:chemistry / Q000378:metabolism
D000606:Amino Sugars; D006027:Glycosides; D037102:Lectins; C117670:N-acetylleucinamide; C032269:sialyl-N-acetyllactosamine; D001710:Biotin; D012799:Sialyltransferases; C029156:N-acetyllactosaminide alpha-2,3-sialyltransferase; D001616:beta-Galactosidase; D007930:Leucine