Enzymatic synthesis of sialyl-Lewis(a)-libraries with two non-natural monosaccharide units.
A series of sialylated type-I sugars, which have the natural N-acetyl group of the glucosamine moiety replaced by a wide range of amides, is incubated with recombinant fucosyl-transferase III and non-natural guanosine-diphosphate activated donor-sugars. Surprisingly, the enzyme tolerates the simultaneous alterations on the donor and acceptor to form a wide array of sialyl-Lewis(a)-analogues.
Baisch
G
G
Novartis Pharma AG, Schwarzwaldallee, Basle, Switzerland.
Ohrlein
R
R
Streiff
M
M
Kolbinger
F
F
D000577:Amides; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D019992:Databases as Topic; D005647:Fucosyltransferases / Q000378:metabolism*; D005732:Gangliosides / Q000138:chemical synthesis* / Q000737:chemistry; D005944:Glucosamine / Q000378:metabolism; D006156:Guanosine Diphosphate Sugars; D008958:Models, Molecular; D008969:Molecular Sequence Data; D009005:Monosaccharides / Q000737:chemistry / Q000378:metabolism; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011994:Recombinant Proteins / Q000378:metabolism; D013329:Structure-Activity Relationship; D013379:Substrate Specificity
D000577:Amides; D005732:Gangliosides; D006156:Guanosine Diphosphate Sugars; D009005:Monosaccharides; D009844:Oligosaccharides; D011994:Recombinant Proteins; C093287:di-sialyl Le(a); D005647:Fucosyltransferases; C019818:3-galactosyl-N-acetylglucosaminide 4-alpha-L-fucosyltransferase; D005944:Glucosamine