Modular synthesis of photocleavable peptides using click chemistry

被引：6

作者：

Baccile, Joshua A. ^{[1
]}

Morrell, Mark A. ^{[1
]}

Falotico, Ross M. ^{[1
]}

Milliken, Brandon T. ^{[1
]}

Drew, Daniel L. ^{[1
]}

Rossi, Francis M. ^{[1
]}

机构：

[1] SUNY Coll Cortland, Dept Chem, Cortland, NY 13045 USA

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 15期

关键词：

Click chemistry; Caged compounds; Cell-penetrating peptides; Photocleavable linkers; MOLECULAR TRANSPORTERS; CELLULAR UPTAKE; KINASE-ACTIVITY; CYCLOADDITION; DERIVATIVES; SELECTIVITY; SURFACES; DELIVERY; DESIGN; CELLS;

D O I：

10.1016/j.tetlet.2012.02.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A modular synthesis of photocleavable peptides was developed. Peptide based kinase substrates were modified on solid support with a traceless linker derived from 1-(2-nitrophenyl)propargyl alcohol and coupled to azide functionalized cell-penetrating peptides using Cu(I) catalyzed click chemistry. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：1933 / 1935

页数：3

共 41 条

[1] Suborganelle Sensing of Mitochondrial cAMP-Dependent Protein Kinase Activity [J].

Agnes, Richard S. ;

Jernigan, Finith ;

Shell, Jennifer R. ;

Sharma, Vyas ;

Lawrence, David S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) :6075-6080

[2] Design and synthesis of a photocleavable biotin-linker for the photoisolation of ligand-receptor complexes based on the photolysis of 8-quinolinyl sulfonates in aqueous solution [J].

Aoki, Shin ;

Matsuo, Nanako ;

Hanaya, Kengo ;

Yamada, Yasuyuki ;

Kageyama, Yoshiyuki .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (09) :3405-3413

[3] Modifications in the chemical structure of Trojan carriers: impact on cargo delivery [J].

Aussedat, Baptiste ;

Dupont, Edmond ;

Sagan, Sandrine ;

Joliot, Alain ;

Lavielle, Solange ;

Chassaing, Gerard ;

Burlina, Fabienne .

CHEMICAL COMMUNICATIONS, 2008, (12) :1398-1400

[4] Click chemistry with O-dimethylpropargylcarbamate for preparation of pH-sensitive functional groups.: A case study [J].

Bertrand, Philippe ;

Gesson, Jean Pierre .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (09) :3596-3599

[5] Click Chemistry and Bioorthogonal Reactions: Unprecedented Selectivity in the Labeling of Biological Molecules [J].

Best, Michael D. .

BIOCHEMISTRY, 2009, 48 (28) :6571-6584

[6] Photochemical cleavage of leader peptides [J].

Bindman, Noah ;

Merkx, Remco ;

Koehler, Robert ;

Herrman, Nicholas ;

van der Donk, Wilfred A. .

CHEMICAL COMMUNICATIONS, 2010, 46 (47) :8935-8937

[7] Conjugation of an oligonucleotide to Tat, a cell-penetrating peptide, via click chemistry [J].

Brown, Sarah D. ;

Graham, Duncan .

TETRAHEDRON LETTERS, 2010, 51 (38) :5032-5034

[8] Molecular transporters for peptides:: delivery of a cardioprotective εPKC agonist peptide into cells and intact ischemic heart using a transport system, R7 [J].

Chen, L ;

Wright, LR ;

Chen, CH ;

Oliver, SF ;

Wender, PA ;

Mochly-Rosen, D .

CHEMISTRY & BIOLOGY, 2001, 8 (12) :1123-1129

[9]

Demko ZP, 2002, ANGEW CHEM INT EDIT, V41, P2113, DOI 10.1002/1521-3773(20020617)41:12<2113::AID-ANIE2113>3.0.CO

[10]

2-Q

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