Evaluation of the molecular interactions of fluorinated amino acids with native polypepticles

被引:52
作者
Jäckel, C [1 ]
Seufert, W [1 ]
Thust, S [1 ]
Koksch, B [1 ]
机构
[1] Univ Leipzig, Dept Organ Chem, D-04103 Leipzig, Germany
关键词
amino acids; coiled-coil peptides; fluorine; helical structures; protein modifications; self replication;
D O I
10.1002/cbic.200300840
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
One fluorine can make a difference. Investigation of the properties of fluorinated amino acids in a native-polypeptide environment increases our ability to use this class of non-natural amino acids for protein engineering. Two fluorinated amino acids (see figure) were incorporated into different positions of a heptad repeat motif, and their influence on coiled-coil peptide formation was studied. The screens introduced here are sufficiently sensitive to even detect the difference of one single fluorine atom in the side chain of an amino acid.
引用
收藏
页码:717 / 720
页数:4
相关论文
共 26 条
[11]  
Koksch B, 1997, J PEPT SCI, V3, P157, DOI 10.1002/(SICI)1099-1387(199705)3:3<157::AID-PSC94>3.0.CO
[12]  
2-W
[13]   Observation of intramolecular C-H•••F-C contacts in non-metallocene polyolefin catalysts:: Model for weak attractive interactions between polymer chain and noninnocent ligand [J].
Kui, SCF ;
Zhu, NY ;
Chan, MCW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (14) :1628-1632
[14]  
KUI SCF, 2003, ANGEW CHEM, V115, P1666
[15]  
MUIR TW, 1997, CURR OPIN BIOTECH, V4, P420
[16]   REACTIONS OF TRIFLUOROMETHYL KETONES .9. INVESTIGATION OF THE STERIC EFFECT OF A TRIFLUOROMETHYL GROUP BASED ON THE STEREOCHEMISTRY ON THE DEHYDRATION OF TRIFLUOROMETHYL HOMOALLYL ALCOHOLS [J].
NAGAI, T ;
NISHIOKA, G ;
KOYAMA, M ;
ANDO, A ;
MIKI, T ;
KUMADAKI, I .
JOURNAL OF FLUORINE CHEMISTRY, 1992, 57 (1-3) :229-237
[17]   A chiroselective peptide replicator [J].
Saghatelian, A ;
Yokobayashi, Y ;
Soltani, K ;
Ghadiri, MR .
NATURE, 2001, 409 (6822) :797-801
[18]   A synthetic peptide ligase [J].
Severin, K ;
Lee, DH ;
Kennan, AJ ;
Ghadiri, MR .
NATURE, 1997, 389 (6652) :706-709
[19]   Stabilization of coiled-coil peptide domains by introduction of trifluoroleucine [J].
Tang, Y ;
Ghirlanda, G ;
Vaidehi, N ;
Kua, J ;
Mainz, DT ;
Goddard, WA ;
DeGrado, WF ;
Tirrell, DA .
BIOCHEMISTRY, 2001, 40 (09) :2790-2796
[20]  
Tang Y, 2001, ANGEW CHEM INT EDIT, V40, P1494, DOI 10.1002/1521-3773(20010417)40:8<1494::AID-ANIE1494>3.0.CO