5-[(Hydroxymethyl)-O-pyrophosphoryl]uracil, an intermediate in the biosynthesis of alpha-putrescinylthymine in deoxyribonucleic acid of bacteriophage phi W-14

Biochemistry. 1981 Jun 9;20(12):3586-91. doi: 10.1021/bi00515a043.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacteriophages / metabolism*
  • Cell-Free System
  • DNA Replication
  • DNA, Viral / biosynthesis*
  • Kinetics
  • Pseudomonas / metabolism*
  • Thymine / analogs & derivatives*
  • Thymine / biosynthesis
  • Uracil / analogs & derivatives*
  • Uracil / metabolism
  • Virus Replication

Substances

  • DNA, Viral
  • alpha-putrescinylthymine
  • Uracil
  • 5-((hydroxymethyl)-O-pyrophosphoryl)uracil
  • Thymine