{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,8]],"date-time":"2026-02-08T04:09:40Z","timestamp":1770523780587,"version":"3.49.0"},"reference-count":28,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2019,2,6]],"date-time":"2019-02-06T00:00:00Z","timestamp":1549411200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002341","name":"Academy of Finland","doi-asserted-by":"publisher","award":["251539, 256214 and 308931"],"award-info":[{"award-number":["251539, 256214 and 308931"]}],"id":[{"id":"10.13039\/501100002341","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Glycosidic (\u03b2-1\u2032\u2032\u21926, 3\u2032 and 4\u2032) site isomers of neomycin B (i.e., neobiosamine (\u03b2-1\u2032\u2032\u21926, 3\u2032 and 4\u2032) neamines) have been synthesized in a straightforward manner. Peracetylated neomycin azide was used as a common starting material to obtain neobiosamine glycosyl donor and 6, 3\u2032,4\u2032-tri-O-acetyl neamine azide that after simple protecting group manipulation was converted to three different glycosyl acceptors (i.e., 5,6,4\u2032-, 5,3\u2032,4\u2032- and 5,6,3\u2032-tri-O-acetyl neamine azide). Glycosylation between the neobiosamine glycosyl donor and the neamine-derived acceptors gave the protected pseudo-tetrasaccharides, which were converted, via global deprotection (deacetylation and reduction of the azide groups), to the desired site isomers of neomycin. The effect of these aminoglycosides on the RNA and DNA triplex stability was studied by UV-melting profile analysis.<\/jats:p>","DOI":"10.3390\/molecules24030580","type":"journal-article","created":{"date-parts":[[2019,2,6]],"date-time":"2019-02-06T11:51:12Z","timestamp":1549453872000},"page":"580","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Synthesis of Glycosidic (\u03b2-1\u2032\u2032\u21926, 3\u2032 and 4\u2032) Site Isomers of Neomycin B and Their Effect on RNA and DNA Triplex Stability"],"prefix":"10.3390","volume":"24","author":[{"given":"Lotta","family":"Granqvist","sequence":"first","affiliation":[{"name":"Department of Chemistry, University of Turku, 20014 Turku, Finland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ville","family":"T\u00e4htinen","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Turku, 20014 Turku, Finland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Pasi","family":"Virta","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Turku, 20014 Turku, Finland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2019,2,6]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1171","DOI":"10.1021\/cr0681546","article-title":"Targeting of RNA with Small Molecules","volume":"108","author":"Thomas","year":"2008","journal-title":"Chem. 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