title: Enzymatic synthesis of tumor-associated carbohydrate antigen Globo-H hexasaccharide.
abstract: 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.
authors.affiliation: Departments of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio 43210, USA.
authors.forename: Doris M
authors.initials: DM
authors.lastname: Su
authors.forename: Hironobu
authors.initials: H
authors.lastname: Eguchi
authors.forename: Wen
authors.initials: W
authors.lastname: Yi
authors.forename: Lei
authors.initials: L
authors.lastname: Li
authors.forename: Peng G
authors.initials: PG
authors.lastname: Wang
authors.forename: Chengfeng
authors.initials: C
authors.lastname: Xia
mesh_terms: 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
chemical_list: 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