{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,2]],"date-time":"2025-11-02T08:31:11Z","timestamp":1762072271206,"version":"build-2065373602"},"reference-count":72,"publisher":"MDPI AG","issue":"21","license":[{"start":{"date-parts":[[2022,10,26]],"date-time":"2022-10-26T00:00:00Z","timestamp":1666742400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Ministry of Education, Science, and Technological Development of the Republic of Serbia","award":["451-03-68\/2022-14\/200124","451-03-68\/2022-14\/200017"],"award-info":[{"award-number":["451-03-68\/2022-14\/200124","451-03-68\/2022-14\/200017"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Although many antibiotics are active against Gram-positive bacteria, fewer also show activity against Gram-negative bacteria. Here, we present a combination of in silico (electron ion-interaction potential, molecular docking, ADMET), NMR, and microbiological investigations of selected macrolides (14-membered, 15-membered, and 16-membered), aiming to discover the pattern of design for macrolides active against Gram-negative bacteria. Although the conformational studies of 14-membered and 15-membered macrolides are abundant in the literature, 16-membered macrolides, and their most prominent representative tylosin A, have received relatively little research attention. We therefore report the complete 1H and 13C NMR assignment of tylosin A in deuterated chloroform, as well as its 3D solution structure determined through molecular modelling (conformational search) and 2D ROESY NMR. Additionally, due to the degradation of tylosin A in deuterated chloroform, other species were also detected in 1D and 2D NMR spectra. We additionally studied the anti-bacterial activity of tylosin A and B against selected Gram-positive and Gram-negative bacteria.<\/jats:p>","DOI":"10.3390\/molecules27217280","type":"journal-article","created":{"date-parts":[[2022,10,26]],"date-time":"2022-10-26T09:59:37Z","timestamp":1666778377000},"page":"7280","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Computational Studies on Selected Macrolides Active against Escherichia coli Combined with the NMR Study of Tylosin A in Deuterated Chloroform"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1248-5864","authenticated-orcid":false,"given":"Biljana","family":"Arsic","sequence":"first","affiliation":[{"name":"Division of Pharmacy and Optometry, School of Health Sciences, University of Manchester, Oxford Road, Manchester M13 9PT, UK"},{"name":"Department of Chemistry, Faculty of Sciences and Mathematics, University of Nis, Visegradska 33, 18000 Nis, Serbia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5424-0291","authenticated-orcid":false,"given":"Jill","family":"Barber","sequence":"additional","affiliation":[{"name":"Division of Pharmacy and Optometry, School of Health Sciences, University of Manchester, Oxford Road, Manchester M13 9PT, UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8101-089X","authenticated-orcid":false,"given":"Ana","family":"Cikos","sequence":"additional","affiliation":[{"name":"NMR Centre, Ru\u0111er Bo\u0161kovi\u0107 Institute, Bijeni\u010dka Cesta 54, 10000 Zagreb, Croatia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8450-4211","authenticated-orcid":false,"given":"Manikandan","family":"Kadirvel","sequence":"additional","affiliation":[{"name":"Division of Pharmacy and Optometry, School of Health Sciences, University of Manchester, Oxford Road, Manchester M13 9PT, UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Emilija","family":"Kostic","sequence":"additional","affiliation":[{"name":"Faculty of Medicine, University of Nis, Bulevar dr Zorana Djindjica 81, 18000 Nis, Serbia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5255-5425","authenticated-orcid":false,"given":"Andrew J.","family":"McBain","sequence":"additional","affiliation":[{"name":"Division of Pharmacy and Optometry, School of Health Sciences, University of Manchester, Oxford Road, Manchester M13 9PT, UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7783-6218","authenticated-orcid":false,"given":"Jelena","family":"Milicevic","sequence":"additional","affiliation":[{"name":"Laboratory for Bioinformatics and Computational Chemistry, Vinca Institute of Nuclear Sciences, National Institute of the Republic of Serbia, The University of Belgrade, Mike Petrovica Alasa 12-14, 11351 Belgrade, Serbia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0519-4556","authenticated-orcid":false,"given":"Angela","family":"Oates","sequence":"additional","affiliation":[{"name":"Centre for Biomedicine, Hull York Medical School, Faculty of Health Sciences, University of Hull, Hull HU6 7RX, UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andrew","family":"Regan","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,10,26]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Arsic, B., Novak, P., Kragol, G., Barber, J., Rimoli, M.G., and Sodano, F. 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