239477-64-6Relevant articles and documents
Structure-function studies on nucleoside antibiotic mureidomycin A: Synthesis of 5′-functionalised uridine models
Gentle, Caragh A.,Harrison, Stephen A.,Inukai, Masatoshi,Bugg, Timothy D. H.
, p. 1287 - 1294 (2007/10/03)
The importance of functional groups in nucleoside antibiotic mureidomycin A (MRD A) for biological activity has been examined by derivatisation of samples of the natural product, and by synthesis of uridine-containing analogues. N-Succinyl and di- and tri-acetyl derivatives MRD A have been prepared, and were found to have reduced activity as inhibitors of E. coli translocase I. The enamide alkene of MRD A was found to be extremely resistant towards hydrogenation by a variety of reagents. Several 5′-functionalised uridine derivatives were synthesised from N3-p-methoxybenzyl-2′,3′-isopropylideneuridine. A series of 5′-aminoacyl derivatives were prepared, and the 3-aminopropionyl (IC50 260 μM) and 7-aminoheptanoyl (IC50 1.5 mM) derivatives were found to act as reversible inhibitors. An analogue mimicking the carboxy terminus of MRD A was synthesised, and also acted as an inhibitor of translocase I (IC50 1.9 mM). A phosphonate analogue designed as a possible suicide inhibitor showed modest inhibition (IC50 3.7 mM), which was shown to be irreversible.
