Convenient enzymatic synthesis of a p-nitrophenyl oligosaccharide series of sialyl N-acetyllactosamine, sialyl Le x and relevant compounds.
From the beta-D-Gal-(1-->4)-beta-D-GlcNAc-OC6H4NO2-p (1) prepared by the transglycosylation of beta-galactosidase from Bacillus circulans, alpha-D-Neu5Ac-(2-->3)-beta-D-Gal-(1-->4)-beta-D-GlcNAc-OC6H4NO2-p (9) and alpha-D-Neu5Ac-(2-->6)-beta-D-Gal-(1-->4)-beta-D-GlcNAc-OC6H4NO2-p (10) were effectively synthesized with an equimolar ratio of CMP-Neu5Ac by recombinant rat alpha-(2-->3)-N-sialyltransferase and rat liver alpha-(2-->6)-N-sialyltransferase, respectively. The former enzyme also transferred effectively the Neu5Ac residue from CMP-Neu5Ac to the location of OH-3 in the non-reducing terminal of beta-D-Gal-(1-->4)-beta-D-Gal-OC6H4NO2-p or beta-D-Gal-(1-->4)-beta-D-Gal-(1-->4)-beta-D-GlcNAc-OC6H4NO2-p, while the latter enzyme did not. In the case of equimolar ratio of GDP-Fuc/acceptor, 1 and 9 were further fucosylated quantitatively to form beta-D-Gal-(1-->4)-beta-D-(alpha-l-Fuc-(1-->3)-)-GlcNAc-OC6H4NO2-p (14) and alpha-D-Neu5Ac-(2-->3)-beta-D-Gal-(1-->4)-beta-D-(alpha-l-Fuc-(1-->3)-)-GlcNAc-OC6H4NO2-p (13) by recombinant human alpha-(1-->3)-fucosyltransferase VII, respectively.
Zeng
Xiaoxiong
X
Research Center of Advanced Bionics, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, 1-1-1 Higashi, Tsukuba 305-8565, Japan.
Uzawa
Hirotaka
H
D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D001407:Bacillus / Q000201:enzymology; D002240:Carbohydrate Sequence; D005647:Fucosyltransferases / Q000737:chemistry; D006801:Humans; D007983:Lewis Blood Group Antigens; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009596:Nitrophenols / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D051381:Rats; D011994:Recombinant Proteins / Q000235:genetics; D000080506:Sialyl Lewis X Antigen; D012799:Sialyltransferases / Q000737:chemistry; D014166:Transferases / Q000737:chemistry*; D001616:beta-Galactosidase / Q000737:chemistry*
D000606:Amino Sugars; D007983:Lewis Blood Group Antigens; C494219:Lewis a oligosaccharide; D009596:Nitrophenols; D009844:Oligosaccharides; D011994:Recombinant Proteins; D000080506:Sialyl Lewis X Antigen; C032269:sialyl-N-acetyllactosamine; D014166:Transferases; C502597:FUT7 protein, human; D005647:Fucosyltransferases; D012799:Sialyltransferases; D001616:beta-Galactosidase