Dynamic Combinatorial Chemistry Employing Boronic Acids/Boronate Esters Leads to Potent Oxygenase Inhibitors

被引：66

作者：

Demetriades, Marina ^{[2
]}

Leung, Ivanhoe K. H. ^{[2
]}

Chowdhury, Rasheduzzaman ^{[2
]}

Chan, Mun Chiang ^{[2
]}

McDonough, Michael A. ^{[2
]}

Yeoh, Kar Kheng ^{[2
]}

Tian, Ya-Min ^{[3
]}

Claridge, Timothy D. W. ^{[2
]}

Ratcliffe, Peter J. ^{[3
]}

Woon, Esther C. Y. ^{[1
]}

Schofield, Christopher J. ^{[2
]}

机构：

[1] Natl Univ Singapore, Dept Pharm, Singapore 117543, Singapore

[2] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England

[3] Univ Oxford, Nuffield Dept Clin Med, Oxford OX3 7BN, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 27期

关键词：

boron; combinatorial chemistry; mass spectrometry; oxygenase; prolyl hydroxylase; MASS-SPECTROMETRY LEADS; BINDING INTERACTIONS; ACID;

D O I：

10.1002/anie.201202000

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dynamic duo: The reversible reaction of boronic acids with alcohols to form boronate esters, coupled to protein mass spectrometry analyses, was used to discover potent oxygenase inhibitors. This dynamic combinatorial mass spectrometry technique could potentially be applied to the identification of other protein inhibitors. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：6672 / 6675

页数：4

共 19 条

[1] Bertini I., 2008, ANGEW CHEM, V120, P4609
[2] Water-based ligand screening for paramagnetic metalloproteins
Bertini, Ivano
Fragai, Marco
Luchinat, Claudio
Talluri, Eleonora
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (24) : 4533 - 4537
[3] Brown T., 2009, THESIS U OXFORD UK
[4] Structural Basis for Binding of Hypoxia-Inducible Factor to the Oxygen-Sensing Prolyl Hydroxylases
Chowdhury, Rasheduzzaman
McDonough, Michael A.
Mecinovic, Jasmin
Loenarz, Christoph
Flashman, Emily
Hewitson, Kirsty S.
Domene, Carmen
Schofield, Christopher J.
[J]. STRUCTURE, 2009, 17 (07) : 981 - 989
[5] Dynamic combinatorial chemistry
Corbett, Peter T.
Leclaire, Julien
Vial, Laurent
West, Kevin R.
Wietor, Jean-Luc
Sanders, Jeremy K. M.
Otto, Sijbren
[J]. CHEMICAL REVIEWS, 2006, 106 (09) : 3652 - 3711
[6] Quantitative determination of noncovalent binding interactions using soft ionization mass spectrometry
Daniel, JM
Friess, SD
Rajagopalan, S
Wendt, S
Zenobi, R
[J]. INTERNATIONAL JOURNAL OF MASS SPECTROMETRY, 2002, 216 (01) : 1 - 27
[7] ARENEBORONATES FROM DIOLS AND POLYOLS
KUIVILA, HG
KEOUGH, AH
SOBOCZENSKI, EJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1954, 19 (05) : 780 - 783
[8] An approach to enzyme inhibition employing reversible boronate ester formation
Leung, Ivanhoe K. H.
Brown, Tom, Jr.
Schofield, Christopher J.
Claridge, Timothy D. W.
[J]. MEDCHEMCOMM, 2011, 2 (05) : 390 - 395
[9] Using NMR Solvent Water Relaxation to Investigate Metalloenzyme-Ligand Binding Interactions
Leung, Ivanhoe K. H.
Flashman, Emily
Yeoh, Kar Kheng
Schofield, Christopher J.
Claridge, Timothy D. W.
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (02) : 867 - 875
[10] Combined mass spectrometry and dynamic chemistry approach to identify metalloenzyme inhibitors
Lienard, Benoft M. R.
Selevsek, Nathalie
Oldham, Neil J.
Schofield, Christopher J.
[J]. CHEMMEDCHEM, 2007, 2 (02) : 175 - +

← 1 2 →