The preparation of 5-cyanouracil and 5-cyano-2'-deoxyuridine from the corresponding 5-iodo derivative and cuprous cyanide.
5-Cyanouracil has been prepared in high yield from cuprous cyanide and 5-iodouracil. The deoxynucleoside has been similarly prepared form 5-iodo-2'-deoxyuridine and this has enabled these compounds to be labelled with (14-C) cyanide. Attempts have been made to incorporate 5-cyanouracil into Escherichia coli 15T and into Mycoplasma mycoides var. capri DNA under conditions in which several other 5-substituted uracils have been incorporated, but without success. Similarly 5-cyano-2'-deoxyuridine could not be incorporated into the DNA of T3 phage under conditions in which 5-bromo-2'-deoxyuridine is easily incorporated. These results suggest that the criteria for a 5-substituted uracil to be incorporated into DNA in vivo depends on some factor other than the size of the substituent.
D055598:Chemical Phenomena; D002621:Chemistry; D003090:Coliphages / Q000378:metabolism; D003486:Cyanides; D004269:DNA, Bacterial / Q000096:biosynthesis; D004279:DNA, Viral / Q000096:biosynthesis; D003857:Deoxyuridine / Q000031:analogs & derivatives*; D004926:Escherichia coli / Q000378:metabolism; D007065:Idoxuridine; D009176:Mycoplasma mycoides / Q000378:metabolism; D009570:Nitriles / Q000378:metabolism; D013329:Structure-Activity Relationship; D014498:Uracil / Q000031:analogs & derivatives* / Q000378:metabolism
D003486:Cyanides; D004269:DNA, Bacterial; D004279:DNA, Viral; D009570:Nitriles; D014498:Uracil; D007065:Idoxuridine; D003857:Deoxyuridine