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. 2019 Jan 25;9:767. doi: 10.1038/s41598-018-36987-9

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© The Author(s) 2019

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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Experimental investigation of the N⁺-CH···O hydrogen bonds focusing on the G9a-like protein (GLP)-inhibitor complex. (A) X-ray structure of GLP complexed with 14a (PDB ID: 3MO0). This figure shows 14a (ball-and-stick) and amino acid residues (stick) within a 5 Å radius from the nitrogen atom of 14a. (B) Schematic diagram of the binding mode between 14a and GLP. The red dotted lines indicate C-H···O hydrogen bonds. (C) Geometry profile for the N⁺-C-H···O contacts between GLP and 14a. The X-ray structure of GLP complexed with inhibitor 14a suggests that the C-H groups adjacent to the nitrogen atom in the dimethylamino group of 14a engage in three C-H···O hydrogen bonds with the Asp1131 and Asp1135 residues of GLP. The hydrogen atom of the ammonium cation does not form any hetero hydrogen bonds. (D) Chemical structures of 14a–d. (E) In vitro GLP-inhibitory activity of 14a–d. ^aValues represent mean values of at least three experiments.