title: Expanding the fluorous arsenal: tetrafluorinated phenylalanines for protein design.
abstract: Tetrafluorinated phenylalanines were incorporated into villin headpiece subdomain HP35, and their energetic contribution to protein stability was evaluated. In comparison to pentafluoro-phenylalanines, HP35 variants harboring tetrafluorinated phenylalanines exhibit increased thermal and thermodynamic stability by a large margin. The favorable stabilization is attributed to the electrostatic ArH...pi interactions retained and strengthened by the highly, but not fully, fluorinated aromatic rings.
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467-3801, USA.
authors.forename: Hong
authors.initials: H
authors.lastname: Zheng
authors.forename: Kristofer
authors.initials: K
authors.lastname: Comeforo
authors.forename: Jianmin
authors.initials: J
authors.lastname: Gao
mesh_terms: D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000737:chemistry*; D008840:Microfilament Proteins / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D017433:Protein Structure, Secondary; D017434:Protein Structure, Tertiary; D013816:Thermodynamics
chemical_list: D006845:Hydrocarbons, Fluorinated; D008840:Microfilament Proteins; C026615:villin; D010649:Phenylalanine