title: Facile synthesis of tetrafluorotyrosine and its application in pH triggered membrane lysis.
abstract: "Smart" peptides that lyse membranes in response to biological stimuli are of considerable interest. Herein, we report a facile synthesis of L-tetrafluorotyrosine (L-f(4)Y) and its utilization as a pH sensing element. The synthetic route affords gram quantities of L-f(4)Y within two days. Incorporation of this unnatural amino acid into magainin 2 gives a peptide that turns on its membrane-lytic activity upon mild acidification.
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467-3801, USA.
authors.forename: Fang
authors.initials: F
authors.lastname: Wang
authors.forename: Luoheng
authors.initials: L
authors.lastname: Qin
authors.forename: Patrick
authors.initials: P
authors.lastname: Wong
authors.forename: Jianmin
authors.initials: J
authors.lastname: Gao
mesh_terms: D002462:Cell Membrane / Q000187:drug effects*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D008958:Models, Molecular; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D017386:Sequence Homology, Amino Acid; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006845:Hydrocarbons, Fluorinated; D010455:Peptides; C556061:tetrafluorotyrosine; D014443:Tyrosine