Facile synthesis of covalent probes to capture enzymatic intermediates during E1 enzyme catalysis

被引：23

作者：

An, Heeseon ^{[1
]}

Statsyuk, Alexander V. ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Ctr Mol Innovat & Drug Discovery, Chem Life Processes Inst, Silverman Hall,2145 Sheridan Rd, Evanston, IL 60208 USA

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 12期

关键词：

UBIQUITIN-LIKE PROTEINS; ACTIVATING ENZYME; SUMO E1; AUTOPHAGY; INSIGHTS; DEHYDROALANINE; DIUBIQUITIN; THERAPY; ATG8;

D O I：

10.1039/c5cc08592f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report a facile synthetic strategy to prepare UBL-AMP electrophilic probes that form a covalent bond with the catalytic cysteine of cognate E1s, mimicking the tetrahedral intermediate of the E1-UBL-AMP complex. These probes enable the structural and biochemical study of both canonical-and non-canonical E1s.

引用

页码：2477 / 2480

页数：4

共 21 条

[1] An inhibitor of ubiquitin conjugation and aggresome formation [J].

An, Heeseon ;

Statsyuk, Alexander V. .

CHEMICAL SCIENCE, 2015, 6 (09) :5235-5245

[2] Crystal Structure of the Human Ubiquitin-activating Enzyme 5 (UBA5) Bound to ATP MECHANISTIC INSIGHTS INTO A MINIMALISTIC E1 ENZYME [J].

Bacik, John-Paul ;

Walker, John R. ;

Ali, Mohsin ;

Schimmer, Aaron D. ;

Dhe-Paganon, Sirano .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2010, 285 (26) :20273-20280

[3] Chemoenzymatic ubiquitination of artificial substrates [J].

Burchak, Olga N. ;

Jaquinod, Michel ;

Cottin, Claire ;

Mugherli, Laurent ;

Iwai, Kazuhiro ;

Chatelain, Francois ;

Balakirev, Maxim Y. .

CHEMBIOCHEM, 2006, 7 (11) :1667-+

[4] Methods for converting cysteine to dehydroalanine on peptides and proteins [J].

Chalker, Justin M. ;

Gunnoo, Smita B. ;

Boutureira, Omar ;

Gerstberger, Stefanie C. ;

Fernandez-Gonzalez, Marta ;

Bernardes, Goncalo J. L. ;

Griffin, Laura ;

Hailu, Hanna ;

Schofield, Christopher J. ;

Davis, Benjamin G. .

CHEMICAL SCIENCE, 2011, 2 (09) :1666-1676

[5] SYNTHESIS OF PROTEINS BY NATIVE CHEMICAL LIGATION [J].

DAWSON, PE ;

MUIR, TW ;

CLARKLEWIS, I ;

KENT, SBH .

SCIENCE, 1994, 266 (5186) :776-779

[6] Chemical Synthesis of Ubiquitin, Ubiquitin-Based Probes, and Diubiquitin [J].

El Oualid, Farid ;

Merkx, Remco ;

Ekkebus, Reggy ;

Hameed, Dharjath S. ;

Smit, Judith J. ;

de Jong, Annemieke ;

Hilkmann, Henk ;

Sixma, Titia K. ;

Ovaa, Huib .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (52) :10149-10153

[7] Dehydroalanine-Based Diubiquitin Activity Probes [J].

Haj-Yahya, Najat ;

Hemantha, Hosahalli P. ;

Meledin, Roman ;

Bondalapati, Somasekhar ;

Seenaiah, Mallikanti ;

Brik, Ashraf .

ORGANIC LETTERS, 2014, 16 (02) :540-543

[8] Origin and function of ubiquitin-like proteins [J].

Hochstrasser, Mark .

NATURE, 2009, 458 (7237) :422-429

[9] Autophagy as a target for anticancer therapy [J].

Janku, Filip ;

McConkey, David J. ;

Hong, David S. ;

Kurzrock, Razelle .

NATURE REVIEWS CLINICAL ONCOLOGY, 2011, 8 (09) :528-539

[10] Structures of the SUMO E1 provide mechanistic insights into SUMO activation and E2 recruitment to E1 [J].

Lois, LM ;

Lima, CD .

EMBO JOURNAL, 2005, 24 (03) :439-451

← 1 2 3 →