Enzymatic synthesis of tumor-associated carbohydrate antigen Globo-H hexasaccharide.
We report the enzymatic synthesis of an important tumor-associated carbohydrate antigen, Globo-H hexasaccharide. Starting with Lac-OBn as the initial acceptor, this approach employs three glycosyltransferases: LgtC, an alpha1,4-galactosyltransferase; LgtD, a bifunctional beta1,3-galactosyl/beta1,3-N-acetylgalactosaminyltransferase; and WbsJ, an alpha1,2-fucosyltransferase. In addition, two epimerases, GalE and WbgU, were also employed for the generation of more expensive sugar nucleotides, UDP-Gal and UDP-GalNAc, from their corresponding inexpensive C4 epimers. This study represents a facile enzymatic synthesis of the Globo-H antigen.
Su
Doris M
DM
Departments of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio 43210, USA.
Eguchi
Hironobu
H
Yi
Wen
W
Li
Lei
L
Wang
Peng G
PG
Xia
Chengfeng
C
D015295:Antigens, Tumor-Associated, Carbohydrate / Q000096:biosynthesis* / Q000737:chemistry; D002240:Carbohydrate Sequence; D005647:Fucosyltransferases / Q000378:metabolism; D005700:Galactosyltransferases / Q000378:metabolism*; D006193:Haemophilus influenzae / Q000201:enzymology; D007785:Lactose / Q000737:chemistry*; D017350:N-Acetylgalactosaminyltransferases / Q000378:metabolism; D009345:Neisseria meningitidis / Q000201:enzymology
C527601:1-benzyl-lactose; D015295:Antigens, Tumor-Associated, Carbohydrate; C472765:Globo-H; D005647:Fucosyltransferases; D005700:Galactosyltransferases; D017350:N-Acetylgalactosaminyltransferases; C045097:UDP-galactose-lactosylceramide alpha 1-4-galactosyltransferase; D007785:Lactose