title: Photocleavage of the polypeptide backbone by 2-nitrophenylalanine.
abstract: Photocleavage of the polypeptide backbone is potentially a powerful and general method to activate or deactivate functional peptides and proteins with high spatial and temporal resolution. Here we show that 2-nitrophenylalanine is able to photochemically cleave the polypeptide backbone by an unusual cinnoline-forming reaction. This unnatural amino acid was genetically encoded in E. coli, and protein containing 2-nitrophenylalanine was expressed and site-specifically photocleaved.
authors.affiliation: Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, CA 92037, USA.
authors.forename: Francis B
authors.initials: FB
authors.lastname: Peters
authors.forename: Ansgar
authors.initials: A
authors.lastname: Brock
authors.forename: Jiangyun
authors.initials: J
authors.lastname: Wang
authors.forename: Peter G
authors.initials: PG
authors.lastname: Schultz
mesh_terms: D019943:Amino Acid Substitution; D017122:Bacteriophage T4 / Q000201:enzymology / Q000235:genetics; D004926:Escherichia coli / Q000235:genetics; D009113:Muramidase / Q000737:chemistry / Q000235:genetics / Q000378:metabolism; D010455:Peptides / Q000737:chemistry / Q000378:metabolism; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000235:genetics / Q000378:metabolism; D010777:Photochemistry; D015202:Protein Engineering; D011506:Proteins / Q000737:chemistry / Q000235:genetics* / Q000378:metabolism*; D014764:Viral Proteins / Q000737:chemistry / Q000235:genetics / Q000378:metabolism
chemical_list: C540473:2-nitrophenylalanine; D010455:Peptides; D011506:Proteins; D014764:Viral Proteins; D010649:Phenylalanine; D009113:Muramidase