Divergent Chemoenzymatic Synthesis of Asymmetrical‐Core‐Fucosylated and Core‐Unmodified N‐Glycans |
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Authors: | Dr. Lin Liu Dr. Shuo Wang Prof. Dr. Kelley W. Moremen Prof. Dr. Geert‐Jan Boons |
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Affiliation: | 1. Complex Carbohydrate Research Center, University of Georgia, Athens, Georgia, USA;2. Chemical Biology and Drug Discovery, Utrecht University, Utrecht, The Netherlands |
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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 LewisX epitope to give easy access to core‐unmodified compounds. |
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Keywords: | asymmetrical synthesis bioorganic chemistry chemoenzymatic synthesis glycosylation N-glycans |
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