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


ABSTRACT: 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.

SUBMITTER: John AA 

PROVIDER: S-EPMC4685939 | BioStudies | 2015-01-01T00:00:00Z

REPOSITORIES: biostudies

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