8-Vinylguanine nucleo amino acid: a fluorescent PNA building block

Org Lett. 2012 Mar 16;14(6):1382-5. doi: 10.1021/ol3000603. Epub 2012 Feb 27.

Abstract

Attachment of a vinyl group at guanine position 8 provides fluorescent properties of the nucleobase. Therefore, 8-vinylguanine was introduced as a 2-aminoethylglycine peptide nucleic acid (PNA) building block. Incorporation of the guanine analog in short PNA sequences by Fmoc solid phase peptide synthesis allowed the differentiation between hybridization states of specific double strands with DNA, RNA, and PNA as well as quadruplex forming RNA/PNA oligomers based on fluorescence intensity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • DNA / chemistry
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Guanine / chemistry*
  • Nucleic Acid Hybridization
  • Peptide Nucleic Acids / chemical synthesis
  • Peptide Nucleic Acids / chemistry*
  • RNA / chemistry

Substances

  • Amino Acids
  • Fluorescent Dyes
  • Peptide Nucleic Acids
  • Guanine
  • RNA
  • DNA