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

verfasst von

Thomas Jöge, Martin Jesberger, Patrick Bröker, Andreas Kirschning

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.

Organisationseinheit(en)

Institut für Organische Chemie
Zentrum für Biomolekulare Wirkstoffe (BMWZ)

Typ

Artikel

Journal

Carbohydrate Research

Band

342

Seiten

1704-1714

Anzahl der Seiten

11

ISSN

0008-6215

Publikationsdatum

18.05.2007

Publikationsstatus

Veröffentlicht

Peer-reviewed

Ja

ASJC Scopus Sachgebiete

Analytische Chemie, Biochemie, Organische Chemie

Ziele für nachhaltige Entwicklung

SDG 3 – Gute Gesundheit und Wohlergehen

Elektronische Version(en)

https://doi.org/10.1016/j.carres.2007.05.015 (Zugang: Unbekannt)