Chemoenzymatic iterative synthesis of difficult linkages of oligosaccharides on soluble polymeric supports.
[reaction: see text]. A trisaccharide donor containing a cis-Galpalpha(1-->4)Galp linkage was prepared using a synthetic strategy based on chemoenzymatic oligosaccharide synthesis on a soluble polymeric support. Significantly, only retaining glycosyltransferases gave complete reactions, whereas inverting enzymes showed little or no activity with poly(ethylene glycol) (MPEG)-bound lactose as an acceptor. The MPEG-attached trisaccharide was shown to bind to Verotoxin-1 by transfer NOE studies through the Galpalpha(1-->4)Galp portion of the molecule.
Yan
F
F
Institute for Biological Sciences, National Research Council of Canada, 100 Sussex Drive, Room 3024, Ottawa, Ontario K1A 0R6, Canada.
Gilbert
M
M
Wakarchuk
W W
WW
Brisson
J R
JR
Whitfield
D M
DM
D002236:Carbohydrate Conformation; D006031:Glycosylation; D016695:Glycosyltransferases / Q000737:chemistry / Q000378:metabolism*; D019906:Nuclear Magnetic Resonance, Biomolecular; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011092:Polyethylene Glycols; D011485:Protein Binding; D022622:Shiga Toxin 1 / Q000378:metabolism; D014312:Trisaccharides / Q000138:chemical synthesis / Q000378:metabolism
D009844:Oligosaccharides; D022622:Shiga Toxin 1; D014312:Trisaccharides; D011092:Polyethylene Glycols; C028210:monomethoxypolyethylene glycol; D016695:Glycosyltransferases