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N-methyl-O-benzylhydroxylamino group at the anomeric position
is an efficient approach to provide alkoxyamino glycosides
stereoselectively in excellent yields with either glycosynthases or
transglycosidases. In addition, it is shown that bulky N-alkyl-O-
benzylhydroxylamino groups offer the opportunity to modulate
the regioselectivity of coupling without the need to mutate
the enzyme active site. Finally, alkoxyamino glycoconjugates can
be easily obtained in aqueous solution without the need for sugar
protecting chemistry and are readily deprotected. They thus pro-
vide a new ‘green’ alternative in the preparation of acceptors for
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This research was supported by a grant from the Region Pays de
la Loire, France (AAP GlycoNet). We gratefully thank David Ropartz
for mass spectrometry analyses and data interpretation. These
analyses were performed within the BIBS platform located at INRA
Nantes (INRA, UR1268 Biopolymères Interactions Assemblages F-
44316 Nantes).
Supplementary data
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Supplementary data (detailed procedures for the preparation of
key intermediates, characterization data) associated with this arti-
References and notes
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