Indium mediated allylation in peptide and protein functionalization

被引:21
作者
Alam, Jenefer [1 ]
Keller, Thomas H. [1 ]
Loh, Teck-Peng [1 ]
机构
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
关键词
UNNATURAL AMINO-ACIDS; N-TERMINAL SERINE; AQUEOUS-SOLUTION; CHEMISTRY; METATHESIS; COMPLEXES;
D O I
10.1039/c1cc12926k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Indium-mediated allylation has been used in the site-selective functionalization of N-terminal aldehydes of peptides and proteins. This is the first demonstration of indium-mediated C-C bond formation in protein labelling studies under mild and environmentally friendly conditions.
引用
收藏
页码:9066 / 9068
页数:3
相关论文
共 29 条
[1]   Functionalization of Peptides and Proteins by Mukaiyama Aldol Reaction [J].
Alam, Jenefer ;
Keller, Thomas H. ;
Loh, Teck-Peng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (28) :9546-9548
[2]   Selective tryptophan modification with rhodium carbenoids in aqueous solution [J].
Antos, JM ;
Francis, MB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) :10256-10257
[3]   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
[4]   ALLYLATION OF CARBONYL-COMPOUNDS WITH CATALYTIC AMOUNT OF INDIUM [J].
ARAKI, S ;
JIN, SJ ;
IDOU, Y ;
BUTSUGAN, Y .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (06) :1736-1738
[5]   Facile conversion of cysteine and alkyl cysteines to dehydroalanine on protein surfaces: Versatile and switchable access to functionalized proteins [J].
Bernardes, Goncalo J. L. ;
Chalker, Justin M. ;
Errey, James C. ;
Davis, Benjamin G. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (15) :5052-+
[6]  
Blackwell HE, 1998, ANGEW CHEM INT EDIT, V37, P3281, DOI 10.1002/(SICI)1521-3773(19981217)37:23<3281::AID-ANIE3281>3.0.CO
[7]  
2-V
[8]   Capture of peptides with N-terminal serine and threonine: A sequence-specific chemical method for peptide mixture simplification [J].
Chelius, D ;
Shaler, TA .
BIOCONJUGATE CHEMISTRY, 2003, 14 (01) :205-211
[9]   Physical stability of proteins in aqueous solution: Mechanism and driving forces in nonnative protein aggregation [J].
Chi, EY ;
Krishnan, S ;
Randolph, TW ;
Carpenter, JF .
PHARMACEUTICAL RESEARCH, 2003, 20 (09) :1325-1336
[10]   Non-canonical amino acids in protein polymer design [J].
Connor, Rebecca E. ;
Tirrell, David A. .
POLYMER REVIEWS, 2007, 47 (01) :9-28