Enantioselective synthesis and application of the highly fluorescent and environment-sensitive amino acid 6-(2-dimethylaminonaphthoyl) alanine (DANA)

被引:60
作者
Nitz, M [1 ]
Mezo, AR [1 ]
Ali, MH [1 ]
Imperiali, B [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1039/b205224e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
6-(2-Dimethylaminonaphthoyl) alanine (DANA) was prepared via an enantioselective synthesis and incorporated into the S-peptide of RNase S establishing the large changes in fluorescence that can occur upon peptide-protein interaction.
引用
收藏
页码:1912 / 1913
页数:2
相关论文
共 36 条
[1]  
Abellán T, 2000, EUR J ORG CHEM, V2000, P2689
[2]  
Cerezo FM, 2001, HELV CHIM ACTA, V84, P3306, DOI 10.1002/1522-2675(20011114)84:11<3306::AID-HLCA3306>3.0.CO
[3]  
2-4
[4]   EFFECTS OF HYDROSTATIC-PRESSURE ON THE LOCATION OF PRODAN IN LIPID BILAYERS AND CELLULAR MEMBRANES [J].
CHONG, PLG .
BIOCHEMISTRY, 1988, 27 (01) :399-404
[5]   Probing protein electrostatics with a synthetic fluorescent amino acid [J].
Cohen, BE ;
McAnaney, TB ;
Park, ES ;
Jan, YN ;
Boxer, SG ;
Jan, LY .
SCIENCE, 2002, 296 (5573) :1700-1703
[6]   THERMODYNAMICS OF PROTEIN PEPTIDE INTERACTIONS IN THE RIBONUCLEASE-S SYSTEM STUDIED BY TITRATION CALORIMETRY [J].
CONNELLY, PR ;
VARADARAJAN, R ;
STURTEVANT, JM ;
RICHARDS, FM .
BIOCHEMISTRY, 1990, 29 (25) :6108-6114
[7]   A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions [J].
Corey, EJ ;
Xu, F ;
Noe, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12414-12415
[8]   A facile protocol for the convenient preparation of amino-substituted α-bromo- and α,α-dibromo arylmethylketones [J].
Diwu, ZJ ;
Beachdel, C ;
Klaubert, DH .
TETRAHEDRON LETTERS, 1998, 39 (28) :4987-4990
[9]   Design of a fluorescent amino acid derivative usable in peptide synthesis [J].
Dufau, I ;
Mazarguil, H .
TETRAHEDRON LETTERS, 2000, 41 (32) :6063-6066
[10]   A nonempirical method using LC/MS for determination of the absolute configuration of constituent amino acids in a peptide: Elucidation of limitations of Marfey's method and of its separation mechanism [J].
Fujii, K ;
Ikai, Y ;
Mayumi, T ;
Oka, H ;
Suzuki, M ;
Harada, K .
ANALYTICAL CHEMISTRY, 1997, 69 (16) :3346-3352