Fluorine in a native protein environment -: How the spatial demand and polarity of fluoroalkyl groups affect protein folding

被引:132
作者
Jaeckel, Christian [1 ]
Salwiczek, Mario [1 ]
Koksch, Beate [1 ]
机构
[1] Free Univ Berlin, Dept Chem & Biochem, D-14195 Berlin, Germany
关键词
amino acids; fluorine; fluorous effect; peptides; protein modification;
D O I
10.1002/anie.200504387
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Give and take: The influence of fluoro substitution of amino acid side chains on their interaction profile in a native polypeptide environment was studied systematically. The fluorination of alkyl groups has opposing electrostatic and steric consequences for the stability of hydrophobic protein cores. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4198 / 4203
页数:6
相关论文
共 38 条
[1]   The polar hydrophobicity of fluorinated compounds [J].
Biffinger, JC ;
Kim, HW ;
DiMagno, SG .
CHEMBIOCHEM, 2004, 5 (05) :622-627
[2]   De novo design of defined helical bundles in membrane environments [J].
Bilgiçer, B ;
Kumar, K .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (43) :15324-15329
[3]   Programmed self-sorting of coiled coils with leucine and hexafluoroleucine cores [J].
Bilgiçer, B ;
Xing, X ;
Kumar, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (47) :11815-11816
[4]   A coiled coil with a fluorous core [J].
Bilgiçer, B ;
Fichera, A ;
Kumar, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) :4393-4399
[5]   SYNTHESIS OF PROTEINS BY NATIVE CHEMICAL LIGATION [J].
DAWSON, PE ;
MUIR, TW ;
CLARKLEWIS, I ;
KENT, SBH .
SCIENCE, 1994, 266 (5186) :776-779
[6]   Organic fluorine: Odd man out [J].
Dunitz, JD .
CHEMBIOCHEM, 2004, 5 (05) :614-621
[7]   Halogenation of drugs enhances membrane binding and permeation [J].
Gerebtzoff, G ;
Li-Blatter, X ;
Fischer, H ;
Frentzel, A ;
Seelig, A .
CHEMBIOCHEM, 2004, 5 (05) :676-684
[8]   Φ-Values beyond the ribosomally encoded amino acids:: Kinetic and thermodynamic consequences of incorporating trifluoromethyl amino acids in a globular protein [J].
Horng, JC ;
Raleigh, DP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (31) :9286-9287
[9]   Solid phase synthesis of peptide C-terminal thioesters by Fmoc/t-Bu chemistry [J].
Ingenito, R ;
Bianchi, E ;
Fattori, D ;
Pessi, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) :11369-11374
[10]   Fluorine in peptide design and protein engineering [J].
Jäckel, C ;
Koksch, B .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (21) :4483-+