Synthesis of Glycosidic (β-1′′→6, 3′ and 4′) Site Isomers of Neomycin B and their Effect on RNA and DNA Triplex Stability
| Autor: | Pasi Virta, Ville Tähtinen, Lotta Granqvist |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Glycosylation
Stereochemistry Pharmaceutical Science 010402 general chemistry 01 natural sciences Article Analytical Chemistry groove binders lcsh:QD241-441 chemistry.chemical_compound Isomerism lcsh:Organic chemistry Drug Discovery medicine Transition Temperature Glycosyl Physical and Theoretical Chemistry Glycosyl donor Protecting group ta116 Chromatography High Pressure Liquid Neamine chemistry.chemical_classification aminoglycosides DNA- and RNA-triple helices 010405 organic chemistry Organic Chemistry Glycosidic bond DNA Neomycin Anti-Bacterial Agents 0104 chemical sciences 3. Good health chemistry Chemistry (miscellaneous) Nucleic Acid Conformation RNA Molecular Medicine Azide Framycetin medicine.drug |
| Zdroj: | Molecules Volume 24 Issue 3 Molecules, Vol 24, Iss 3, p 580 (2019) |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules24030580 |
| Popis: | Glycosidic (&beta 1&prime &prime &rarr 6, 3&prime and 4&prime ) site isomers of neomycin B (i.e., neobiosamine (&beta ) 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&prime 4&prime tri-O-acetyl neamine azide that after simple protecting group manipulation was converted to three different glycosyl acceptors (i.e., 5,6,4&prime 5,3&prime and 5,6,3&prime 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. |
| Databáze: | OpenAIRE |
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