TY - JOUR
T1 - Fluorinated amino acids
T2 - Compatibility with native protein structures and effects on protein–protein interactions
AU - Salwiczek, Mario
AU - Nyakatura, Elisabeth K.
AU - Gerling, Ulla I.M.
AU - Ye, Shijie
AU - Koksch, Beate
PY - 2012/2/27
Y1 - 2012/2/27
N2 - Fluorinated analogues of the canonical α-L-amino acids have gained widespread attention as building blocks that may endow peptides and proteins with advantageous biophysical, chemical and biological properties. This critical review covers the literature dealing with investigations of peptides and proteins containing fluorinated analogues of the canonical amino acids published over the course of the past decade including the late nineties. It focuses on side-chain fluorinated amino acids, the carbon backbone of which is identical to their natural analogues. Each class of amino acids—aliphatic, aromatic, charged and polar as well as proline—is presented in a separate section. General effects of fluorine on essential properties such as hydrophobicity, acidity/basicity and conformation of the specific side chains and the impact of these altered properties on stability, folding kinetics and activity of peptides and proteins are discussed (245 references).
AB - Fluorinated analogues of the canonical α-L-amino acids have gained widespread attention as building blocks that may endow peptides and proteins with advantageous biophysical, chemical and biological properties. This critical review covers the literature dealing with investigations of peptides and proteins containing fluorinated analogues of the canonical amino acids published over the course of the past decade including the late nineties. It focuses on side-chain fluorinated amino acids, the carbon backbone of which is identical to their natural analogues. Each class of amino acids—aliphatic, aromatic, charged and polar as well as proline—is presented in a separate section. General effects of fluorine on essential properties such as hydrophobicity, acidity/basicity and conformation of the specific side chains and the impact of these altered properties on stability, folding kinetics and activity of peptides and proteins are discussed (245 references).
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U2 - 10.1039/c1cs15241f
DO - 10.1039/c1cs15241f
M3 - Article
C2 - 22130572
AN - SCOPUS:84857536069
SN - 0306-0012
VL - 41
SP - 2135
EP - 2171
JO - Chemical Society Reviews
JF - Chemical Society Reviews
IS - 6
ER -