Nucleoside, antibiotics kinases

Showdomycin. Showdomycin (2-p-D-ribofuranosyhnaleimide) (7) is a maleimide C-nucleoside antibiotic synthesi2ed by S. showdoensis-, isoshowdomycin (8) and maleimycin (9) have also been isolated (1—6). Showdomycin is not phosphorylated by nucleoside kinase and is not a substrate for nucleoside phosphorylase. Once (7) enters the cell, it blocks the uptake of glucose and other nutrients. 

Uridine has been converted in seven steps into 5 -amino-3, 5 -dideoxyuridine (66), related to the 4, 5 -unsaturated structure found in the mureidomycin antibiotics. Some 5 -Amino-5 -deoxy-5-iodo-pyrrolopyrimidine nucleosides such as 67 (X = Cl, NH2) have been prepared by sodium salt glycosylation procedures, and shown to be powerful adenosine kinase inhibitors. ... 

Treatment of adenosine with sodium toluene-p-sulphinate and sodium hypochlorite gives a 50% yield of 2 -0-tosyladenosine. iV-Chloro intermediates are thought to be involved, which then give tosyl chloride by reaction with the sulphinate, but it is unclear why this procedure gives a higher yield than direct tosylation.229 Amino acids linked to (deoxy)-nucleosides via a sulphamoyl group have been reported they are structurally similar to the antibiotic ascamycin (see also Vol. 23, p.226).230 3. and 5 -0-dansyl derivatives of thymidine have been prepared, and shown to act as inhibitors of thymidine kinase from herpes simplex virus.231... 

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