title: Divergent Chemoenzymatic Synthesis of Asymmetrical-Core-Fucosylated and Core-Unmodified N-Glycans.
abstract: A divergent chemoenzymaytic approach for the preparation of core-fucosylated and core-unmodified asymmetrical N-glycans from a common advances precursor is described. An undecasaccharide was synthesized by sequential chemical glycosylations of an orthogonally protected core fucosylated hexasaccharide that is common to all mammalian core fucosylated N-glycans. Antennae-selective enzymatic extension of the undecasaccharide using a panel of glycosyl transferases afforded core fucosylated asymmetrical triantennary N-glycan isomers, which are potential biomarkers for breast cancer. A unique aspect of our approach is that a fucosidase (FucA1) has been identified that selectively can cleave a core-fucoside without affecting the fucoside of a sialyl LewisXepitope to give easy access to core-unmodified compounds.
authors: Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, Georgia, 30602, USA.
authors: Tiehai
authors: T
authors: Li
authors: Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, Georgia, 30602, USA.
authors: Min
authors: M
authors: Huang
authors: Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, Georgia, 30602, USA.
authors: Lin
authors: L
authors: Liu
authors: Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, Georgia, 30602, USA.
authors: Shuo
authors: S
authors: Wang
authors: Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, Georgia, 30602, USA.
authors: Kelley W
authors: KW
authors: Moremen
authors: Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, Georgia, 30602, USA.|Chemical Biology and Drug Discovery, Utrecht University, Universiteitsweg 99, 3584 CG, Utrecht, The Netherlands.
authors: Geert-Jan
authors: http://orcid.org/0000-0003-3111-5954
authors: GJ
authors: Boons
mesh_terms: D000818:Animals; D000939:Epitopes / Q000737:chemistry*; D006031:Glycosylation; D006801:Humans; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D005644:alpha-L-Fucosidase / Q000737:chemistry*
chemical_list: D000939:Epitopes; D011134:Polysaccharides; D005644:alpha-L-Fucosidase
keywords: N-glycans; asymmetrical synthesis; bioorganic chemistry; chemoenzymatic synthesis; glycosylation