Premium
Divergent Chemoenzymatic Synthesis of Asymmetrical‐Core‐Fucosylated and Core‐Unmodified N ‐Glycans
Author(s) -
Li Tiehai,
Huang Min,
Liu Lin,
Wang Shuo,
Moremen Kelley W.,
Boons GeertJan
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604999
Subject(s) - glycan , cleave , chemistry , glycosylation , core (optical fiber) , glycosyl , fucosidase , fucose , epitope , biochemistry , enzyme , biology , galactose , glycoprotein , antibody , materials science , immunology , composite material
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 Lewis X epitope to give easy access to core‐unmodified compounds.