Selective labeling of polypeptides using protein farnesyltransferase via rapid oxime ligation

被引：25

作者：

Rashidian, Mohammad ^{[1
]}

Dozier, Jonathan K. ^{[1
]}

Lenevich, Stepan ^{[1
]}

Distefano, Mark D. ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

来源：

CHEMICAL COMMUNICATIONS | 2010年 / 46卷 / 47期

关键词：

CHEMISTRY; IMMOBILIZATION; CELLS;

D O I：

10.1039/c0cc03305g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An aldehyde-containing alternative substrate for protein farnesyltransferase was prepared and shown to be enzymatically incorporated into a peptide and a protein. The protein was subsequently immobilized onto aminooxy-functionalized agarose beads or labeled with a fluorophore. This method for protein modification provides an alternative to the commonly employed Cu(I)-catalyzed click reaction.

引用

页码：8998 / 9000

页数：3

共 15 条

[1] Tetrazine ligation: Fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity [J].

Blackman, Melissa L. ;

Royzen, Maksim ;

Fox, Joseph M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) :13518-+

[2] Nucleophilic catalysis of oxime ligation [J].

Dirksen, Anouk ;

Hackeng, Tilman M. ;

Dawson, Philip E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (45) :7581-7584

[3] Selective labeling of proteins by using protein farnesyltransferase [J].

Duckworth, Benjamin P. ;

Zhang, Zhiyuan ;

Hosokawa, Ayako ;

Distefano, Mark D. .

CHEMBIOCHEM, 2007, 8 (01) :98-105

[4] Site-specific, covalent attachment of proteins to a solid surface [J].

Duckworth, Benjamin P. ;

Xu, Juhua ;

Taton, T. Andrew ;

Guo, Athena ;

Distefano, Mark D. .

BIOCONJUGATE CHEMISTRY, 2006, 17 (04) :967-974

[5] Regio- and chemoselective covalent immobilization of proteins through unnatural amino acids [J].

Gauchet, Cecile ;

Labadie, Guillermo R. ;

Poulter, C. Dale .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (29) :9274-9275

[6]

Kolb HC, 2001, ANGEW CHEM INT EDIT, V40, P2004, DOI 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.3.CO

[7]

2-X

[8] Cuprate-mediated synthesis and biological evaluation of cyclopropyl- and tert-butylfarnesyl diphosphate analogs [J].

Mu, YQ ;

Gibbs, RA ;

Eubanks, LM ;

Poulter, CD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8010-8015

[9] Exploiting the substrate tolerance of farnesyltransferase for site-selective protein derivatization [J].

Nguyen, Uyen T. T. ;

Cramer, Janina ;

Gomis, Joaquin ;

Reents, Reinhard ;

Gutierrez-Rodriguez, Marta ;

Goody, Roger S. ;

Alexandrov, Kirill ;

Waldmann, Herbert .

CHEMBIOCHEM, 2007, 8 (04) :408-423

[10] Chemistry in living systems [J].

Prescher, JA ;

Bertozzi, CR .

NATURE CHEMICAL BIOLOGY, 2005, 1 (01) :13-21

← 1 2 →