Details
| Original language | English |
|---|---|
| Pages (from-to) | 1704-1714 |
| Number of pages | 11 |
| Journal | Carbohydrate Research |
| Volume | 342 |
| Issue number | 12-13 |
| Publication status | Published - 18 May 2007 |
Abstract
The synthesis of spacer-linked neoaminoglycoside 5 is described. Key steps of the synthesis are the introduction of nitrogen functionalities at C-3 and C-6 and the olefin cross metathesis of allyl glycoside 16. Although it is known that Grubbs catalysts tolerate nitrogen functionalities, difficulties were encountered in the cross metathesis reaction. Factors that govern this dimerization are the steric and electronic demands of the catalyst and the substrate. Preliminary biological evaluation of homodimer 5, by studying the inhibition of HIV-1 TAR-RNA/Tat-peptide complex using a method based on fluorescence titration, revealed an inhibitory effect of 5.
Keywords
- Aminoglycosides, Antibiotics, Azidosugars, Olefin metathesis
ASJC Scopus subject areas
- Chemistry(all)
- Analytical Chemistry
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Organic Chemistry
Sustainable Development Goals
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In: Carbohydrate Research, Vol. 342, No. 12-13, 18.05.2007, p. 1704-1714.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthetic access to spacer-linked 3,6-diamino-2,3,6-trideoxy-α-d-glucopyranosides-potential aminoglycoside mimics for the inhibition of the HIV-1 TAR-RNA/Tat-peptide complex
AU - Jöge, Thomas
AU - Jesberger, Martin
AU - Bröker, Patrick
AU - Kirschning, Andreas
N1 - Funding information: This work was supported by the Deutsche Forschungsgemeinschaft (SFB 416, project B2) and by the Fonds der Chemischen Industrie. We thank J. Alves (Medical University Hannover, MHH) for helpful support with respect to fluorescence titration.
PY - 2007/5/18
Y1 - 2007/5/18
N2 - The synthesis of spacer-linked neoaminoglycoside 5 is described. Key steps of the synthesis are the introduction of nitrogen functionalities at C-3 and C-6 and the olefin cross metathesis of allyl glycoside 16. Although it is known that Grubbs catalysts tolerate nitrogen functionalities, difficulties were encountered in the cross metathesis reaction. Factors that govern this dimerization are the steric and electronic demands of the catalyst and the substrate. Preliminary biological evaluation of homodimer 5, by studying the inhibition of HIV-1 TAR-RNA/Tat-peptide complex using a method based on fluorescence titration, revealed an inhibitory effect of 5.
AB - The synthesis of spacer-linked neoaminoglycoside 5 is described. Key steps of the synthesis are the introduction of nitrogen functionalities at C-3 and C-6 and the olefin cross metathesis of allyl glycoside 16. Although it is known that Grubbs catalysts tolerate nitrogen functionalities, difficulties were encountered in the cross metathesis reaction. Factors that govern this dimerization are the steric and electronic demands of the catalyst and the substrate. Preliminary biological evaluation of homodimer 5, by studying the inhibition of HIV-1 TAR-RNA/Tat-peptide complex using a method based on fluorescence titration, revealed an inhibitory effect of 5.
KW - Aminoglycosides
KW - Antibiotics
KW - Azidosugars
KW - Olefin metathesis
UR - http://www.scopus.com/inward/record.url?scp=34447341990&partnerID=8YFLogxK
U2 - 10.1016/j.carres.2007.05.015
DO - 10.1016/j.carres.2007.05.015
M3 - Article
C2 - 17562328
AN - SCOPUS:34447341990
VL - 342
SP - 1704
EP - 1714
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
IS - 12-13
ER -