Synthesis of cyclic -1,4-oligo-N-acetylglucosamine 'cyclokasaodorin' via a one-pot electrochemical polyglycosylation-isomerization-cyclization process
Chemical Communications(2022)
Abstract
Electrochemical synthesis of unnatural cyclic oligosaccharides composed of N-acetylglucosamine with alpha-1,4-glycosidic linkages has been accomplished. A thioglycoside monomer equipped with the 2,3-oxazolidinone protecting group was used to prepare linear oligosaccharides by electrochemical polyglycosylation. In the same pot, isomerization of the linear oligosaccharides and intramolecular electrochemical glycosylation for cyclization were also conducted sequentially to obtain the precursor of the cyclic alpha-1,4-oligo-N-acetylglucosamine 'cyclokasaodorin'.
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Key words
Oligosaccharide Synthesis,Enzymatic Glycoside Synthesis,Glycosylation Mechanisms,Asymmetric Catalysis,Glycoprotein Synthesis
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