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Wiley, Chemistry - A European Journal, 52(22), p. 18742-18746, 2016

DOI: 10.1002/chem.201604999

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Divergent Chemoenzymatic Synthesis of Asymmetrical-Core-Fucosylated and Core-Unmodified N-Glycans

Journal article published in 2016 by Tiehai Li, Min Huang, Lin Liu, Shuo Wang, Kelley W. Moremen, Geert-Jan Boons ORCID
This paper is available in a repository.
This paper is available in a repository.

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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 Lewis(X) epitope to give easy access to core-unmodified compounds.