title: Alkoxyamino glycoside acceptors for the regioselective synthesis of oligosaccharides using glycosynthases and transglycosidases.
abstract: Alkoxyamino derivatives of oligosaccharides have been synthesized by enzymatic synthesis using a glycosynthase and a transglycosidase. The chemoselective assembly of unprotected oligosaccharides bearing glucose at the reducing end with N-alkyl-O-benzylhydroxylamine provides sugar derivatives that are good acceptors for enzymatic synthesis using either glycosynthase or transglycosidase. Furthermore, this method affords the possibility of controlling the regioselectivity of coupling depending on the nature of the alkoxyamino substituent and provides high-yield coupling of sugars without the need for complex protecting group chemistry.
authors.affiliation: LUNAM Université, Université de Nantes, CNRS FRE n°3478, UFIP, 2 rue de la Houssinière, F-44322 Nantes cedex 03, France.
authors.forename: David
authors.initials: D
authors.lastname: Teze
authors.forename: Michel
authors.initials: M
authors.lastname: Dion
authors.forename: Franck
authors.initials: F
authors.lastname: Daligault
authors.forename: Vinh
authors.initials: V
authors.lastname: Tran
authors.forename: Corinne
authors.initials: C
authors.lastname: André-Miral
authors.forename: Charles
authors.initials: C
authors.lastname: Tellier
mesh_terms: D000438:Alcohols / Q000737:chemistry; D005959:Glucosidases / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*; D006027:Glycosides / Q000737:chemistry* / Q000378:metabolism; D006031:Glycosylation; D015394:Molecular Structure; D009154:Mutation; D009844:Oligosaccharides / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000438:Alcohols; D006027:Glycosides; D009844:Oligosaccharides; C059688:alkoxyl radical; D005959:Glucosidases