Synthesis and Site-Specific Incorporation of Red-Shifted Azobenzene Amino Acids into Proteins

نویسندگان

  • Alford A. John
  • Carlo P. Ramil
  • Yulin Tian
  • Gang Cheng
  • Qing Lin
چکیده

A series of red-shifted azobenzene amino acids were synthesized in moderate-to-excellent yields via a two-step procedure in which tyrosine derivatives were first oxidized to the corresponding quinonoidal spirolactones followed by ceric ammonium nitrate-catalyzed azo formation with the substituted phenylhydrazines. The resulting azobenzene-alanine derivatives exhibited efficient trans/cis photoswitching upon irradiation with a blue (448 nm) or green (530 nm) LED light. Moreover, nine superfolder green fluorescent protein (sfGFP) mutants carrying the azobenzene-alanine analogues were expressed in E. coli in good yields via amber codon suppression with an orthogonal tRNA/PylRS pair, and one of the mutants showed durable photoswitching with the LED light.

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عنوان ژورنال:

دوره 17  شماره 

صفحات  -

تاریخ انتشار 2015