1602771-91-4Relevant academic research and scientific papers
One-pot synthesis of N-acetyl- and N-glycolylneuraminic acid capped trisaccharides and evaluation of their influenza A(H1 N1) inhibition
Hsu, Yun,Ma, Hsiu-Hwa,Lico, Larry S.,Jan, Jia-Tsrong,Fukase, Koichi,Uchinashi, Yosuke,Zulueta, Medel Manuel L.,Hung, Shang-Cheng
supporting information, p. 2413 - 2416 (2014/03/21)
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. Flu the coop: A stereoselective one-pot assembly and divergent transformation enabled the synthesis of six N-acetyl- and N-glycolylneuraminic-acid-capped trisaccharides. Two of the N-glycolylneuraminic-acid-capped trisaccharides showed inhibitory activities against a common human influenza virus. Bz=benzoyl, NIS=N-iodosuccinimide, Tf=trifluoromethanesulfonyl, TMS=trimethylsilyl. Copyright
