tetano
Editor, Senior Moderator
Angew Chem Int Ed Engl. 2014 Jan 31. doi: 10.1002/anie.201309646. [Epub ahead of print]
One-Pot Synthesis of N-Acetyl- and N-Glycolylneuraminic Acid Capped Trisaccharides and Evaluation of Their Influenza A(H1 N1) Inhibition.
Hsu Y, Ma HH, Lico LS, Jan JT, Fukase K, Uchinashi Y, Zulueta MM, **** SC.
Author information
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.
Copyright ? 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
KEYWORDS:
carbohydrates, glycosylation, stereoselectivity, synthetic methods, viruses
PMID:
24482157
[PubMed - as supplied by publisher]
http://www.ncbi.nlm.nih.gov/pubmed/24482157
One-Pot Synthesis of N-Acetyl- and N-Glycolylneuraminic Acid Capped Trisaccharides and Evaluation of Their Influenza A(H1 N1) Inhibition.
Hsu Y, Ma HH, Lico LS, Jan JT, Fukase K, Uchinashi Y, Zulueta MM, **** SC.
Author information
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.
Copyright ? 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
KEYWORDS:
carbohydrates, glycosylation, stereoselectivity, synthetic methods, viruses
PMID:
24482157
[PubMed - as supplied by publisher]
http://www.ncbi.nlm.nih.gov/pubmed/24482157