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One‐Pot Synthesis of N ‐Acetyl‐ and N ‐Glycolylneuraminic Acid Capped Trisaccharides and Evaluation of Their Influenza A(H1 N1) Inhibition
Author(s) -
Hsu Yun,
Ma HsiuHwa,
Lico Larry S.,
Jan JiaTsrong,
Fukase Koichi,
Uchinashi Yosuke,
Zulueta Medel Manuel L.,
Hung ShangCheng
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201309646
Subject(s) - hemagglutinin (influenza) , neuraminic acid , chemistry , sialic acid , influenza a virus , virus , n acetylneuraminic acid , stereoselectivity , virology , biochemistry , biology , catalysis
Abstract Human lung epithelial cells natively offer terminal N ‐acetylneuraminic acid (Neu5Ac) α(2→6)‐linked to galactose (Gal) as binding sites for influenza virus hemagglutinin. N ‐Glycolylneuraminic acid (Neu5Gc) in place of Neu5Ac is known to affect hemagglutinin binding in other species. Not normally generated by humans, Neu5Gc may find its way to human cells from dietary sources. To compare their influence in influenza virus infection, six trisaccharides with Neu5Ac or Neu5Gc α(2→6) linked to Gal and with different reducing end sugar units were prepared using one‐pot assembly and divergent transformation. The sugar assembly made use of an N ‐phthaloyl‐protected sialyl imidate for chemoselective activation and α‐stereoselective coupling with a thiogalactoside. Assessment of cytopathic effect showed that the Neu5Gc‐capped trisaccharides inhibited the viral infection better than their Neu5Ac counterparts.