title: The rapid and facile synthesis of oxyamine linkers for the preparation of hydrolytically stable glycoconjugates.
abstract: The synthesis of a number of N-glycosyl-N-alkyl-methoxyamine bifunctional linkers is described. The linkers contain an N-methoxyamine functional group for conjugation to carbohydrates and a terminal group, such as an amine, azide, thiol, or carboxylic acid, for conjugation to the probe of choice. The strategy for the linker synthesis is rapid (3-4 steps) and efficient (51-96% overall yield), and many of the linkers can be synthesized using a three-step one-pot strategy. Moreover, the linkers can be conjugated to glycans in excellent yield and they show excellent stability toward hydrolytic cleavage.
authors.affiliation: School of Chemical and Physical Sciences, Victoria University of Wellington , P.O. Box 600, Wellington, New Zealand.
authors.forename: Stefan
authors.initials: S
authors.lastname: Munneke
authors.forename: Julien R C
authors.initials: JR
authors.lastname: Prevost
authors.forename: Gavin F
authors.initials: GF
authors.lastname: Painter
authors.forename: Bridget L
authors.initials: BL
authors.lastname: Stocker
authors.forename: Mattie S M
authors.initials: MS
authors.lastname: Timmer
mesh_terms: D020650:Combinatorial Chemistry Techniques; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D006898:Hydroxylamines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011134:Polysaccharides / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D006001:Glycoconjugates; D006898:Hydroxylamines; D011134:Polysaccharides; D013438:Sulfhydryl Compounds; C005214:methoxyamine