1.
Carbohydr Res
; 342(12-13): 1704-14, 2007 Sep 03.
Article
in English
| MEDLINE
| ID: mdl-17562328
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.
Subject(s)
Aminoglycosides/chemistry , Aminoglycosides/pharmacology , Anti-HIV Agents/chemical synthesis , Gene Products, tat/drug effects , Glucosides/pharmacology , Glycosides/chemical synthesis , HIV Long Terminal Repeat/drug effects , Aminoglycosides/chemical synthesis , Anti-HIV Agents/pharmacology , Diamines , Gene Products, tat/chemistry , Glucosides/chemical synthesis , Glycosides/pharmacology , HIV/genetics , RNA, Viral/chemistry , RNA, Viral/drug effects , tat Gene Products, Human Immunodeficiency Virus
2.
Angew Chem Int Ed Engl
; 42(10): 1166-70, 2003 Mar 10.
Article
in English
| MEDLINE
| ID: mdl-12640651