Synthesis and properties of the p -Sulfonamide analogue of the green fluorescent protein (GFP) Chromophore: The mimic of GFP chromophore with very strong N-H photoacid strength

Yi Hui Chen, Robert Sung, Kuangsen Sung

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

The para-sulfonamide analogue (p-TsABDI) of a green fluorescent protein (GFP) chromophore was synthesized to mimic the GFP chromophore. Its S1 excited-state pKa value in dimethylsulfoxide (DMSO) is -1.5, which is strong enough to partially protonate dipolar aprotic solvents and causes excited-state proton transfer (ESPT), so it can partially mimic the GFP chromophore to further study the ESPT-related photophysics and the blinking phenomenon of GFP. In comparison with 8-hydroxypyrene-1,3,6-trisulfonate (HPTS) (pKa = 7.4, pKa = 1.3 in water), p-TsABDI (pKa = 6.7, pKa = -1.5 in DMSO) is a better photoacid for pH-jump studies.

Original languageEnglish
Pages (from-to)1768-1772
Number of pages5
JournalOrganic Letters
Volume20
Issue number7
DOIs
Publication statusPublished - 2018 Apr 6

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis and properties of the p -Sulfonamide analogue of the green fluorescent protein (GFP) Chromophore: The mimic of GFP chromophore with very strong N-H photoacid strength'. Together they form a unique fingerprint.

Cite this