Probing Chiral Recognition of Enzyme Active Sites with Octahedral Iridium(III) Propeller Complexes

被引:20
|
作者
Goebel, Peter [1 ]
Ritterbusch, Florian [1 ]
Helms, Melanie [1 ]
Bischof, Matthias [1 ]
Harms, Klaus [1 ]
Jung, Manfred [2 ]
Meggers, Eric [1 ,3 ]
机构
[1] Univ Marburg, Fachbereich Chem, Hans Meerwein Str, D-35043 Marburg, Germany
[2] Univ Freiburg, Inst Pharmaceut Sci, D-79104 Freiburg, Germany
[3] Xiamen Univ, Coll Chem & Chem Engn, Xiamen 361005, Peoples R China
关键词
Enzyme inhibitors; Iridium; Chirality; Molecular recognition; Metal-centered configuration; METAL-COMPLEXES; ORGANOMETALLIC COMPOUNDS; ASYMMETRIC-SYNTHESIS; INHIBITORS; FERROCENE; CHEMISTRY; DISCOVERY; AGENTS; IX;
D O I
10.1002/ejic.201500087
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Chiral bis-cyclometalated octahedral organoiridium(III) complexes were designed to target different classes of enzymes, namely carbonic anhydrases, histone deacetylases, and serine proteases. The stereoselective non-racemic synthesis of selected complexes was used to study the chiral discrimination of enzyme active sites for enantiomers of propeller-type octahedral metal complexes. Cases for negligible, modest, and significant chiral discrimination in the interaction of iridium propeller complexes with enzyme active sites were identified.
引用
收藏
页码:1654 / 1659
页数:6
相关论文
共 50 条
  • [1] Diastereoselective Synthesis of Chiral Octahedral Iridium(III) Phosphano-Oxazoline Complexes
    Carmona, Daniel
    Ferrer, Joaquina
    Garcia, Nestor
    Ramirez, Paola
    Lahoz, Fernando J.
    Garcia-Orduna, Pilar
    Oro, Luis A.
    ORGANOMETALLICS, 2013, 32 (06) : 1595 - 1608
  • [2] Chiral Recognition and Photoreaction β-Amino Acids with Iridium(III) Complexes
    Xiong, Ming-Feng
    Zhou, Hai-Yun
    Huang, Xiao-Kang
    Fan, Jing-Yan
    Ye, Bao-Hui
    CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (24) : 2909 - 2918
  • [3] Chiral Recognition and Dynamic Thermodynamic Resolution of Sulfoxides by Chiral Iridium(III) Complexes
    Yao, Su-Yang
    Chen, Xing-Yang
    Ou, Yan-Ling
    Ye, Bao-Hui
    INORGANIC CHEMISTRY, 2017, 56 (02) : 878 - 885
  • [4] Diphosphinoazine rhodium(III) and iridium(III) octahedral complexes
    Posta, Martin
    Cermak, Jan
    Vojtisek, Pavel
    Sykora, Jan
    Cisarova, Ivana
    INORGANICA CHIMICA ACTA, 2009, 362 (01) : 208 - 216
  • [5] Chiral Octahedral Phosphano-Oxazoline Iridium(III) Complexes as Catalysts in Asymmetric Cycloaddition Reactions
    Carmona, Daniel
    Ferrer, Joaquina
    Garcia, Nestor
    Ramirez, Paola
    Lahoz, Fernando J.
    Garcia-Orduna, Pilar
    Oro, Luis A.
    ORGANOMETALLICS, 2013, 32 (06) : 1609 - 1619
  • [6] Discrepancy between Proline and Homoproline in Chiral Recognition and Diastereomeric Photoreactivity with Iridium(III) Complexes
    Xiong, Ming-Feng
    Peng, He-Long
    Zhang, Xue-Peng
    Ye, Bao-Hui
    INORGANIC CHEMISTRY, 2021, 60 (08) : 5423 - 5431
  • [7] Understanding the Origin of the Chiral Recognition of Esters with Octahedral Chiral Cobalt Complexes
    Jang, Sumin
    Kim, Hyunwoo
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (04) : 886 - 890
  • [8] Asymmetric Nucleophilic Catalysis with an Octahedral Chiral-at-Metal Iridium(III) Complex
    Cruchter, Thomas
    Medvedev, Michael G.
    Shen, Xiaodong
    Mietke, Thomas
    Harms, Klaus
    Marsch, Michael
    Meggers, Eric
    ACS CATALYSIS, 2017, 7 (08): : 5151 - 5162
  • [9] Diastereoselective Photooxidation and Reduction of Chiral Iridium(III) Complexes
    Li, Li-Ping
    Peng, He-Long
    Wei, Lian-Qiang
    Ye, Bao-Hui
    INORGANIC CHEMISTRY, 2019, 58 (01) : 785 - 793
  • [10] Molecular recognition at enzyme active sites
    Diederich, Franois N.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243