18530-85-3Relevant academic research and scientific papers
An efficient synthesis of 3-fluoro-5-thio-xylofuranosyl nucleosides of thymine, uracil, and 5-fluorouracil as potential antitumor or/and antiviral agents
Tsoukala, Evangelia,Agelis, George,Dolinsek, Jan,Botic, Tanja,Cencic, Avrelija,Komiotis, Dimitri
, p. 3241 - 3247 (2007)
1,2:5,6-Di-O-isopropylidene-α-d-glucofuranose by the sequence of mild oxidation, reduction, fluorination, periodate oxidation, borohydride reduction, and sulfonylation gave 3-deoxy-3-fluoro-1,2-O-isopropylidene-5-O-p-toluenesulfonyl-α-d-xy lofuranose (5).
Inhibition of S-ribosylhomocysteinase (LuxS) by substrate analogues modified at the ribosyl C-3 position
Wnuk, Stanislaw F.,Robert, Jenay,Sobczak, Adam J.,Meyers, Brandon P.,Malladi, Venkata L.A.,Zhu, Jinge,Gopishetty, Bhaskar,Pei, Dehua
experimental part, p. 6699 - 6706 (2009/12/24)
S-Ribosylhomocysteinase (LuxS) catalyzes the cleavage of the thioether bond of S-ribosylhomocysteine (SRH) to produce homocysteine and 4,5-dihydroxy-2,3-pentanedione (DPD), which is the precursor of type 2 autoinducer for bacterial cell-cell communication. In this work, we have synthesized several SRH analogues modified at the ribose C3 position as potential inhibitors of LuxS. While removal or methylation of the C3-OH resulted in simple competitive inhibitors of moderate potency, inversion of the C3 stereochemistry or substitution of fluorine for C3-OH resulted in slow-binding inhibitors of improved potency. The most potent inhibitor showed a KI* value of 0.43 μM.
