title: 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.
authors.affiliation: Department of Chemistry, State University of New York at Buffalo , Buffalo, New York 14260-3000, United States.
authors.forename: Alford A
authors.initials: AA
authors.lastname: John
authors.affiliation: Department of Chemistry, State University of New York at Buffalo , Buffalo, New York 14260-3000, United States.
authors.forename: Carlo P
authors.initials: CP
authors.lastname: Ramil
authors.affiliation: Department of Chemistry, State University of New York at Buffalo , Buffalo, New York 14260-3000, United States.
authors.forename: Yulin
authors.initials: Y
authors.lastname: Tian
authors.affiliation: Department of Chemistry, State University of New York at Buffalo , Buffalo, New York 14260-3000, United States.
authors.forename: Gang
authors.initials: G
authors.lastname: Cheng
authors.affiliation: Department of Chemistry, State University of New York at Buffalo , Buffalo, New York 14260-3000, United States.
authors.forename: Qing
authors.initials: Q
authors.lastname: Lin
mesh_terms: D000409:Alanine / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D004926:Escherichia coli / Q000737:chemistry; D049452:Green Fluorescent Proteins / Q000235:genetics; D015394:Molecular Structure; D011506:Proteins / Q000737:chemistry*; D012343:RNA, Transfer; D014443:Tyrosine / Q000737:chemistry
chemical_list: D000596:Amino Acids; D001391:Azo Compounds; D011506:Proteins; D049452:Green Fluorescent Proteins; D014443:Tyrosine; D012343:RNA, Transfer; C009850:azobenzene; D000409:Alanine