Synthesis of mono- and dinucleotide photoaffinity probes of ribonucleic acid polymerase

Leslie H. DeRiemer, Claude F. Meares

Research output: Contribution to journalArticlepeer-review

45 Scopus citations


The abortive initiation reaction of RNA polymerase has been used to prepare adenylyl-(3′-5′)-uridine 5′-phosphate (pApU) in 74% yield from AMP and UTP. The reactive intermediate p-azidophenyl phosphorimidazolidate has been prepared by starting from p-nitrophenyl phosphate. Reaction of this compound with the terminal phosphates of adenosine 5′-phosphate and adenylyl-(3′-5′)-uridine 5′-phosphate gives the corresponding β-substituted 5′-diphosphates. These products are incorporated into the 5′ (leading) end of RNA by RNA polymerase (Escherichia coli) and can be photoactivated at a specific stage of RNA elongation. The dinucleotide photoaffinity label β-(4-azidophenyl) adenylyl-(3′-5′)-uridine 5′-diphosphate stimulates RNA synthesis more strongly than adenylyl-(3′-5′)-uridine.

Original languageEnglish (US)
Pages (from-to)1606-1612
Number of pages7
Issue number6
StatePublished - 1981

ASJC Scopus subject areas

  • Biochemistry


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