Synthesis and photochemistry of pH-sensitive GFP chromophore analogs

Alan R. Katritzky, Megumi Yoshioka-Tarver, Bahaa El Dien M. El-Gendy, C. Dennis Hall

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

GFP chromophore analogs (7a-e, 8, and 10a,b) containing 2-thienyl-, 5-methyl-2-furyl-, 2-pyrryl, and 6-methyl-2-pyridyl-groups were synthesized and their fluorescence spectra recorded in the pH range 1-7. NMR studies showed that protonation of 8 (2-thienyl system) inhibited photoisomerization (Z-E) about the exocyclic double bond but that protonation of 7c (E + Z) (2-pyrryl system) gave only 7cE. Fluorescence studies revealed enhancement of fluorescence intensity of 7c and 7b,e (furyl system) below pH 2.5 and gave a similar result for 10a (pyridyl system) below pH 6. Quantum yields at pH 1 were low, probably due to excited state proton transfer (ESPT).

Original languageEnglish
Pages (from-to)2224-2227
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number17
DOIs
StatePublished - Apr 27 2011

Keywords

  • Fluorescence
  • GFP chromophores
  • Hydrogen bonding
  • N NMR
  • Photoisomerization

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