Expanding the fluorous arsenal: tetrafluorinated phenylalanines for protein design

Hong Zheng; Kristofer Comeforo; Jianmin Gao

doi:10.1021/ja8062309

Expanding the fluorous arsenal: tetrafluorinated phenylalanines for protein design

J Am Chem Soc. 2009 Jan 14;131(1):18-9. doi: 10.1021/ja8062309.

Authors

Hong Zheng¹, Kristofer Comeforo, Jianmin Gao

Affiliation

¹ Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467-3801, USA.

PMID: 19067509
DOI: 10.1021/ja8062309

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Hydrocarbons, Fluorinated / chemical synthesis
Hydrocarbons, Fluorinated / chemistry*
Microfilament Proteins / chemical synthesis
Microfilament Proteins / chemistry*
Models, Molecular
Phenylalanine / analogs & derivatives*
Phenylalanine / chemical synthesis
Phenylalanine / chemistry
Protein Structure, Secondary
Protein Structure, Tertiary
Thermodynamics

Substances

Hydrocarbons, Fluorinated
Microfilament Proteins
villin
Phenylalanine