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In 6\u2019\u2010epiapramycin, the trans\u2010nature of the 6\u2019\u2010hydroxy group and the 7\u2019\u2010methylamino group results in a much weaker intramolecular hydrogen bond, and a consequently weaker cooperative hydrogen bonding network with A1408, resulting overall in reduced inhibition of protein synthesis and antibacterial activity.<\/jats:p>","DOI":"10.1002\/cmdc.202200486","type":"journal-article","created":{"date-parts":[[2022,10,5]],"date-time":"2022-10-05T22:24:26Z","timestamp":1665008666000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Importance of Co\u2010operative Hydrogen Bonding in the Apramycin\u2010Ribosomal Decoding A\u2010Site Interaction"],"prefix":"10.1002","volume":"18","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0063-660X","authenticated-orcid":false,"given":"Michael G.","family":"Pirrone","sequence":"first","affiliation":[{"name":"Department of Pharmaceutical and Biomedical Sciences University of Georgia  250 West Green Street 30602 Athens, GA USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7599-894X","authenticated-orcid":false,"given":"Chennaiah","family":"Ande","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical and Biomedical Sciences University of Georgia  250 West Green Street 30602 Athens, GA USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Klara","family":"Haldimann","sequence":"additional","affiliation":[{"name":"Institute of Medical Microbiology University of Zurich  Gloriastrasse 28 8006 Z\u00fcrich Switzerland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9205-0384","authenticated-orcid":false,"given":"Sven N.","family":"Hobbie","sequence":"additional","affiliation":[{"name":"Institute of Medical Microbiology University of Zurich  Gloriastrasse 28 8006 Z\u00fcrich Switzerland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5989-0712","authenticated-orcid":false,"given":"Andrea","family":"Vasella","sequence":"additional","affiliation":[{"name":"Organic Chemistry Institute ETH Z\u00fcrich  Vladimir-Prelog-Weg 1\u20135\/10 8093 Z\u00fcrich Switzerland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2570-0121","authenticated-orcid":false,"given":"Erik C.","family":"B\u00f6ttger","sequence":"additional","affiliation":[{"name":"Institute of Medical Microbiology University of Zurich  Gloriastrasse 28 8006 Z\u00fcrich Switzerland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2400-0083","authenticated-orcid":false,"given":"David","family":"Crich","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical and Biomedical Sciences Department of Chemistry Complex Carbohydrate Research Center University of Georgia  250 West Green Street 30602 Athens, GA USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2022,10,28]]},"reference":[{"key":"e_1_2_6_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00874a003"},{"key":"e_1_2_6_2_1","unstructured":"\u00a0"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1204073109"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1093\/jac\/dky546"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.diagmicrobio.2016.09.002"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.diagmicrobio.2017.03.006"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.3389\/fmicb.2017.02275"},{"key":"e_1_2_6_8_2","first-page":"0096","author":"Galani I.","year":"2018","journal-title":"ECCMID"},{"key":"e_1_2_6_9_2","first-page":"e02585","volume":"62","author":"Kang A. 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