Convenient and Efficient Preparations of Azodye-Labeled Peptides

被引:15
作者
Katritzky, Alan R. [1 ]
Chen, Qi-Yin [1 ]
Tala, Srinivasa R. [1 ]
机构
[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA
关键词
azodye; benzotriazole methodology; N-protected(alpha-aminoacyl)benzotriazole; photoisomerization; small peptides; AMINO-ACIDS; PHOTOBIOLOGICAL SWITCHES; ALPHA-CHYMOTRYPSIN; MOLECULAR BEACONS; TEMPORARY MARKER; BINDING; PHOTOREGULATION; REAGENTS; ASSAY;
D O I
10.1111/j.1747-0285.2009.00813.x
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
N-(4-Arylazobenzoyl)-1H-benzotriazoles 15a, 15b react with dipeptides 12a-d, (12d+12d') and tripeptides 14a, 14b to give azodye labeled-dipeptides (16a-e), (16d+16d'), (16e+16e') and -tripeptides 16f, 16g in high yields (73-93%) with retention of chirality.
引用
收藏
页码:611 / 617
页数:7
相关论文
共 48 条
[1]   Investigation into the P3 binding domain of m-calpain using photoswitchable diazo- and triazene-dipeptide aldehydes:: New anticataract agents [J].
Abell, Andrew D. ;
Jones, Matthew A. ;
Neffe, Axel T. ;
Aitken, Steven G. ;
Cain, Thomas P. ;
Payne, Richard J. ;
McNabb, Stephen B. ;
Coxon, James M. ;
Stuart, Blair G. ;
Pearson, David ;
Lee, Hannah Y. -Y. ;
Morton, James D. .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (12) :2916-2920
[2]   Where to attach dye molecules to a protein: lessons from the computer program WHAT IF [J].
Altenberg-Greulich, B ;
Vriend, G .
JOURNAL OF MOLECULAR STRUCTURE, 2001, 598 (01) :1-8
[3]   Substrate specificity of prostate-specific membrane antigen [J].
Anderson, Marc O. ;
Wu, Lisa Y. ;
Santiago, Nicholas M. ;
Moser, Jamie M. ;
Rowley, Jennifer A. ;
Bolstad, Erin S. D. ;
Berkman, Clifford E. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (21) :6678-6686
[4]   Fluorescence resonance energy transfer between unnatural amino acids in a structurally modified dihydrofolate reductase [J].
Anderson, RD ;
Zhou, J ;
Hecht, SM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (33) :9674-9675
[5]   DNA-dye conjugates for controllable H* aggregation [J].
Asanuma, H ;
Shirasuka, K ;
Takarada, T ;
Kashida, H ;
Komiyama, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (08) :2217-2223
[6]  
Asanuma H, 2001, ANGEW CHEM INT EDIT, V40, P2671, DOI 10.1002/1521-3773(20010716)40:14<2671::AID-ANIE2671>3.0.CO
[7]  
2-Z
[8]  
Behrendt R, 1999, J PEPT SCI, V5, P519, DOI 10.1002/(SICI)1099-1387(199911)5:11<519::AID-PSC223>3.0.CO
[9]  
2-3
[10]   PEPTIDE COUPLING IN THE PRESENCE OF SO-CALLED LIQUID-CRYSTAL FORMERS [J].
CARPINO, LA ;
CHAO, HG ;
NOWSHAD, F ;
SHROFF, H .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) :6139-6144