Synthesis of Glycosidic (β-1′′→6, 3′ and 4′) Site Isomers of Neomycin B and Their Effect on RNA and DNA Triplex Stability
Glycosidic (β-1′′→6, 3′ and 4′) site isomers of neomycin B (i.e., neobiosamine (β-1′′→6, 3′ and 4′) neamines) have been synthesized in a straightforward manner. Peracetylated neomyci...
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-02-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/3/580 |
| _version_ | 1819113325559021568 |
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| author | Lotta Granqvist Ville Tähtinen Pasi Virta |
| author_facet | Lotta Granqvist Ville Tähtinen Pasi Virta |
| author_sort | Lotta Granqvist |
| collection | DOAJ |
| description | Glycosidic (β-1′′→6, 3′ and 4′) site isomers of neomycin B (i.e., neobiosamine (β-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-<i>O</i>-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-<i>O</i>-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. |
| first_indexed | 2024-12-22T04:27:37Z |
| format | Article |
| id | doaj.art-eb38c0c0a4e348758f6c030f30049a8c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-22T04:27:37Z |
| publishDate | 2019-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-eb38c0c0a4e348758f6c030f30049a8c2022-12-21T18:39:08ZengMDPI AGMolecules1420-30492019-02-0124358010.3390/molecules24030580molecules24030580Synthesis of Glycosidic (β-1′′→6, 3′ and 4′) Site Isomers of Neomycin B and Their Effect on RNA and DNA Triplex StabilityLotta Granqvist0Ville Tähtinen1Pasi Virta2Department of Chemistry, University of Turku, 20014 Turku, FinlandDepartment of Chemistry, University of Turku, 20014 Turku, FinlandDepartment of Chemistry, University of Turku, 20014 Turku, FinlandGlycosidic (β-1′′→6, 3′ and 4′) site isomers of neomycin B (i.e., neobiosamine (β-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-<i>O</i>-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-<i>O</i>-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.https://www.mdpi.com/1420-3049/24/3/580aminoglycosidesDNA- and RNA-triple helicesgroove binders |
| spellingShingle | Lotta Granqvist Ville Tähtinen Pasi Virta Synthesis of Glycosidic (β-1′′→6, 3′ and 4′) Site Isomers of Neomycin B and Their Effect on RNA and DNA Triplex Stability Molecules aminoglycosides DNA- and RNA-triple helices groove binders |
| title | Synthesis of Glycosidic (β-1′′→6, 3′ and 4′) Site Isomers of Neomycin B and Their Effect on RNA and DNA Triplex Stability |
| title_full | Synthesis of Glycosidic (β-1′′→6, 3′ and 4′) Site Isomers of Neomycin B and Their Effect on RNA and DNA Triplex Stability |
| title_fullStr | Synthesis of Glycosidic (β-1′′→6, 3′ and 4′) Site Isomers of Neomycin B and Their Effect on RNA and DNA Triplex Stability |
| title_full_unstemmed | Synthesis of Glycosidic (β-1′′→6, 3′ and 4′) Site Isomers of Neomycin B and Their Effect on RNA and DNA Triplex Stability |
| title_short | Synthesis of Glycosidic (β-1′′→6, 3′ and 4′) Site Isomers of Neomycin B and Their Effect on RNA and DNA Triplex Stability |
| title_sort | synthesis of glycosidic β 1 6 3 and 4 site isomers of neomycin b and their effect on rna and dna triplex stability |
| topic | aminoglycosides DNA- and RNA-triple helices groove binders |
| url | https://www.mdpi.com/1420-3049/24/3/580 |
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