5-[(Hydroxymethyl)-O-pyrophosphoryl]uracil, an intermediate in the biosynthesis of alpha-putrescinylthymine in deoxyribonucleic acid of bacteriophage phi W-14.
In a nonpermissive host, an amber mutant, am 37, of bacteriophage phi W-14 synthesizes deoxyribonucleic acid (DNA) of considerably greater buoyant density than the DNA synthesized by wild-type phage. The am 37 DNA lacks the hypermodified pyrimidine, alpha-putrescinylthymine (putThy). Instead, it contains a new modified base, 5-[(hydroxymethyl)-O-pyrophosphoryl]uracil (hmPPUra). Extracts of cells infected with wild-type phi W-14 convert the hmPPUra in am 37 DNA to putThy when incubated with putrescine.
D001435:Bacteriophages / Q000378:metabolism*; D002474:Cell-Free System; D004261:DNA Replication; D004279:DNA, Viral / Q000096:biosynthesis*; D007700:Kinetics; D011549:Pseudomonas / Q000378:metabolism*; D013941:Thymine / Q000031:analogs & derivatives* / Q000096:biosynthesis; D014498:Uracil / Q000031:analogs & derivatives* / Q000378:metabolism; D014779:Virus Replication
D004279:DNA, Viral; C025113:alpha-putrescinylthymine; D014498:Uracil; C031674:5-((hydroxymethyl)-O-pyrophosphoryl)uracil; D013941:Thymine