5′-Amino Pyrene Provides a Sensitive, Nonperturbing Fluorescent Probe of RNA Secondary and Tertiary Structure Formation

Ryszard Kierzek, Yi Li, Douglas H. Turner, Philip C. Bevilacqua

Research output: Contribution to journalArticlepeer-review

74 Scopus citations

Abstract

Blocked phosphoramidites of 5′-amino-5′-deoxycytidine and 5′-amino-5′-deoxyuridine have been prepared and coupled to the 5′-end of oligoribonucleotides. These 5′-amino RNA oligomers may be readily conjugated to a variety of commercially available amine reactive fluorescent dyes, including succinimidyl ester derivatives. The synthesis, purification, and properties of 5′-pyrene-labeled RNA oligomers are described. These oligomers are shown to be unusually attractive probes for studies of oligomer-oligomer and oligomer-ribozyme interactions. In particular, 5′-pyrene oligomers are stable and very sensitive to environment while having minimal perturbations on the thermodynamics of secondary and tertiary structure formation in RNA. Thus the 5′-positioning of pyrene with a short linker appears to provide an ideal probe for the binding and dynamics of RNA substrates.

Original languageEnglish (US)
Pages (from-to)4985-4992
Number of pages8
JournalJournal of the American Chemical Society
Volume115
Issue number12
DOIs
StatePublished - Jun 1 1993

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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