An efficient and concise method to synthesize locked GFP chromophore analogues

Soumit Chatterjee, Peter Karuso

Research output: Contribution to journalArticleResearchpeer-review

Abstract

A series of GFP analogues, which are fluorescent in the solid state at room temperature, but weakly fluorescent in solution, have been synthesized via an oxazolone formation process that involves a condensation reaction in the presence of a Lewis acid following a Knoevenagel condensation. A ring opened intermediate is formed which cyclizes readily upon heating to produce the imidazolinone. This method is faster, simpler and produces higher yields than alternative methods. A few analogues represent locked GFP derivatives where the exocyclic single bond rotation has been stopped. Weak fluorescence, even after stopping single bond rotation, indicates that restriction of conformation is not effectively controlled and that the double bond rotation is solely responsible for the major non-radiative pathway.

LanguageEnglish
Pages5197-5200
Number of pages4
JournalTetrahedron Letters
Volume57
Issue number47
DOIs
Publication statusPublished - 23 Nov 2016

Fingerprint

Chromophores
Oxazolone
Lewis Acids
Condensation reactions
Heating
Conformations
Condensation
Fluorescence
Derivatives
Temperature
single bond

Keywords

  • Fluorescence
  • Green Fluorescent Protein
  • HBDI
  • Knoevenagel condensation
  • Oxazolinone

Cite this

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An efficient and concise method to synthesize locked GFP chromophore analogues. / Chatterjee, Soumit; Karuso, Peter.

In: Tetrahedron Letters, Vol. 57, No. 47, 23.11.2016, p. 5197-5200.

Research output: Contribution to journalArticleResearchpeer-review

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