Palladium-mediated site-selective Suzuki-Miyaura protein modification at genetically encoded aryl halides

被引:108
作者
Spicer, Christopher D. [1 ]
Davis, Benjamin G. [1 ]
机构
[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England
基金
英国生物技术与生命科学研究理事会; 英国工程与自然科学研究理事会;
关键词
NONNATURAL AMINO-ACIDS; MALTOSE-BINDING PROTEIN; CROSS-METATHESIS; IN-VIVO; CHEMISTRY; BIOLOGY; FUNCTIONALITY; PHENYLALANINE; STRATEGIES; PEPTIDES;
D O I
10.1039/c0cc04970k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Site-specific genetic incorporation of unnatural p-halophenylalanine amino acid residues as 'tags' coupled with Pd(0)-mediated Suzuki-Miyuara 'modification' has been enabled by discovery of an effective small molecule palladium scavenger.
引用
收藏
页码:1698 / 1700
页数:3
相关论文
共 27 条
[1]   Transition metal catalyzed methods for site-selective protein modification [J].
Antos, John M. ;
Francis, Matthew B. .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2006, 10 (03) :253-262
[2]   Expanded chemical diversity sampling through whole protein evolution [J].
Baldwin, Amy J. ;
Arpino, James A. J. ;
Edwards, Wayne R. ;
Tippmann, Eric M. ;
Jones, D. Dafydd .
MOLECULAR BIOSYSTEMS, 2009, 5 (07) :764-766
[3]   A Genetically Encoded Boronate-Containing Amino Acid [J].
Brustad, Eric ;
Bushey, Mark L. ;
Lee, Jae Wook ;
Groff, Dan ;
Liu, Wenshe ;
Schultz, Peter G. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (43) :8220-8223
[4]   A Convenient Catalyst for Aqueous and Protein Suzuki-Miyaura Cross-Coupling [J].
Chalker, Justin M. ;
Wood, Charlotte S. C. ;
Davis, Benjamin G. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (45) :16346-+
[5]   Enabling olefin metathesis on proteins: chemical methods for installation of S-allyl cysteine [J].
Chalker, Justin M. ;
Lin, Yuya A. ;
Boutureira, Omar ;
Davis, Benjamin G. .
CHEMICAL COMMUNICATIONS, 2009, (25) :3714-3716
[6]   Chemical Modification of Proteins at Cysteine: Opportunities in Chemistry and Biology [J].
Chalker, Justin M. ;
Bernardes, Goncalo J. L. ;
Lin, Yuya A. ;
Davis, Benjamin G. .
CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (05) :630-640
[7]   Sugars and proteins: New strategies in synthetic biology [J].
Davis, Benjamin G. .
PURE AND APPLIED CHEMISTRY, 2009, 81 (02) :285-298
[8]   Nonnatural Amino Acids for Site-Specific Protein Conjugation [J].
de Graaf, Albert J. ;
Kooijman, Marlous ;
Hennink, Wim E. ;
Mastrobattista, Enrico .
BIOCONJUGATE CHEMISTRY, 2009, 20 (07) :1281-1295
[9]   Single amino acid substitutions on the surface of Escherichia coli maltose-binding protein can have a profound impact on the solubility of fusion proteins [J].
Fox, JD ;
Kapust, RB ;
Waugh, DS .
PROTEIN SCIENCE, 2001, 10 (03) :622-630
[10]   Evolution of Amber Suppressor tRNAs for Efficient Bacterial Production of Proteins Containing Nonnatural Amino Acids [J].
Guo, Jiantao ;
Melancon, Charles E., III ;
Lee, Hyun Soo ;
Groff, Dan ;
Schultz, Peter G. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) :9148-9151