A1 Refereed original research article in a scientific journal
Synthesis of Glycosidic (beta-1 ''-> 6,3 ' and 4 ') Site Isomers of Neomycin B and Their Effect on RNA and DNA Triplex Stability
Authors: Granqvist Lotta, Tähtinen Ville, Virta Pasi
Publisher: MDPI
Publication year: 2019
Journal: Molecules
Journal name in source: MOLECULES
Journal acronym: MOLECULES
Article number: ARTN 580
Volume: 24
Issue: 3
Number of pages: 13
ISSN: 1420-3049
eISSN: 1420-3049
DOI: https://doi.org/10.3390/molecules24030580
Web address : https://www.mdpi.com/1420-3049/24/3/580
Self-archived copy’s web address: https://research.utu.fi/converis/portal/detail/Publication/39636260
Glycosidic (beta-1 ''-> 6, 3' and 4') site isomers of neomycin B (i.e., neobiosamine (beta-1 ''-> 6, 3' and 4') 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',4'-tri-O-acetyl neamine azide that after simple protecting group manipulation was converted to three different glycosyl acceptors (i.e., 5,6,4'-, 5,3',4'- and 5,6,3'-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.
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