A Hydroxyquinoline-Based Unnatural Amino Acid for the Design of Novel Artificial Metalloenzymes

被引:27
作者
Drienovska, Ivana [1 ]
Scheele, Remkes A. [1 ]
Gutierrez de Souza, Cora [1 ]
Roelfes, Gerard [1 ]
机构
[1] Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9747 AG Groningen, Netherlands
基金
欧洲研究理事会;
关键词
biocatalysis; hybrid catalysts; metalloenzymes; noncanonical amino acids; protein design; GENETIC INCORPORATION; COMPUTATIONAL DESIGN; TERMINAL ALKYNES; PROTEIN; COMPLEXES; BINDING; DERIVATIVES; 8-HYDROXYQUINOLINE; METALLOPROTEIN; SITES;
D O I
10.1002/cbic.202000306
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
We have examined the potential of the noncanonical amino acid (8-hydroxyquinolin-3-yl)alanine (HQAla) for the design of artificial metalloenzymes. HQAla, a versatile chelator of late transition metals, was introduced into the lactococcal multidrug-resistance regulator (LmrR) by stop codon suppression methodology. LmrR_HQAla was shown to complex efficiently with three different metal ions, Cu-II, Zn(II)and Rh(III)to form unique artificial metalloenzymes. The catalytic potential of the Cu-II-bound LmrR_HQAla enzyme was shown through its ability to catalyse asymmetric Friedel-Craft alkylation and water addition, whereas the Zn-II-coupled enzyme was shown to mimic natural Zn hydrolase activity.
引用
收藏
页码:3077 / 3081
页数:5
相关论文
共 54 条
[11]   An enantioselective artificial metallo-hydratase [J].
Bos, Jeffrey ;
Garcia-Herraiz, Ana ;
Roelfes, Gerard .
CHEMICAL SCIENCE, 2013, 4 (09) :3578-3582
[12]   Organocatalytic photoreduction of Zn(II) to zinc metal [J].
Brooks, Anthony C. ;
Basore, Katherine ;
Bernhard, Stefan .
CHEMICAL COMMUNICATIONS, 2014, 50 (40) :5196-5199
[13]   Artificial Metalloenzymes: Challenges and Opportunities [J].
Davis, Holly J. ;
Ward, Thomas R. .
ACS CENTRAL SCIENCE, 2019, 5 (07) :1120-1136
[14]   Expanding the enzyme universe with genetically encoded unnatural amino acids [J].
Drienovska, Ivana ;
Roelfes, Gerard .
NATURE CATALYSIS, 2020, 3 (03) :193-202
[15]   A designer enzyme for hydrazone and oxime formation featuring an unnatural catalytic aniline residue [J].
Drienovska, Ivana ;
Mayer, Clemens ;
Dulson, Christopher ;
Roelfes, Gerard .
NATURE CHEMISTRY, 2018, 10 (09) :946-952
[16]   Design of an enantioselective artificial metallo-hydratase enzyme containing an unnatural metal-binding amino acid [J].
Drienovska, Ivana ;
Alonso-Cotchico, Lur ;
Vidossich, Pietro ;
Lledos, Agusti ;
Marechal, Jean-Didier ;
Roelfes, Gerard .
CHEMICAL SCIENCE, 2017, 8 (10) :7228-7235
[17]   Artificial Metalloenzymes for Asymmetric Catalysis by Creation of Novel Active Sites in Protein and DNA Scaffolds [J].
Drienovska, Ivana ;
Roelfes, Gerard .
ISRAEL JOURNAL OF CHEMISTRY, 2015, 55 (01) :21-31
[18]   Novel artificial metalloenzymes by in vivo incorporation of metal-binding unnatural amino acids [J].
Drienovska, Ivana ;
Rioz-Martinez, Ana ;
Draksharapu, Apparao ;
Roelfes, Gerard .
CHEMICAL SCIENCE, 2015, 6 (01) :770-776
[19]   Enantioselective Friedel-Crafts alkylations of α-β-unsaturated 2-acyl imidazoles catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes [J].
Evans, DA ;
Fandrick, KR ;
Song, HJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :8942-8943
[20]   A Chemically Programmed Proximal Ligand Enhances the Catalytic Properties of a Heme Enzyme [J].
Green, Anthony P. ;
Hayashi, Takahiro ;
Mittl, Peer R. E. ;
Hilyert, Donald .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (35) :11344-11352