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. 2017 Aug 15;7:8239. doi: 10.1038/s41598-017-07836-y

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© The Author(s) 2017

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

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Inhibition of avian-origin H5N1 N1 by sulfo-sialic acid analogue 7a. (A) 7a inhibits wildtype N1 with an inhibitory constant (K _i) of 1.62 μM. (B) Predicted binding of 7a to the wildtype N1 active site. (C) 7a inhibits His275Tyr oseltamivir-resistant N1 with a similar potency to that of wildtype N1. (D) Predicted binding of 7a to the His275Tyr N1 active site shows that the 7a glycerol side chain maintains the same interactions with the Glu276 side chain. Key residues relating to His275Tyr drug resistance are shown inside transparent spheres. Electrostatic interactions of the inhibitor sulfo group and glycerol moiety are indicated by dashed lines, with stronger ionic interactions colored orange. The binding analysis was performed with MOE based on the structure of A/Vietnam/1203/04 (H5N1) NA (PDB ID 3CKZ)²⁶.