The Important Role of Halogen Bond in Substrate Selectivity of Enzymatic Catalysis

Jiang, Shuiqin; Zhang, Lujia; Cui, Dongbin; Yao, Zhiqiang; Gao, Bei; Lin, Jian; Wei, Dongzhi

doi:10.1038/srep34750

Cited by 95 publications

(78 citation statements)

References 42 publications

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“…Halogen bonding use has found application in drug biosynthesis as opposed to its traditional exploitations in enabling drug discovery, binding efficacy, and druggability. In a novel study, authors were able to exploit X-bonding in the nitrilase-catalyzed synthesis of ortho -, meta -, and para -chlorophenylacetic acid [ 77 ]. Different distributions of halogen bond induced changes of substrate binding conformation and affected substrate selectivity.…”

Section: Halogen Bonding In Biological Systemsmentioning

confidence: 99%

Looking Back, Looking Forward at Halogen Bonding in Drug Discovery

et al. 2017

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Halogen bonding has emerged at the forefront of advances in improving ligand: receptor interactions. In particular the newfound ability of this extant non-covalent-bonding phenomena has revolutionized computational approaches to drug discovery while simultaneously reenergizing synthetic approaches to the field. Here we survey, via examples of classical applications involving halogen atoms in pharmaceutical compounds and their biological hosts, the unique advantages that halogen atoms offer as both Lewis acids and Lewis bases.

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Section: Halogen Bonding In Biological Systemsmentioning

confidence: 99%

Looking Back, Looking Forward at Halogen Bonding in Drug Discovery

et al. 2017

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“…Halogen bonds are known as the highly directional and specific non‐covalent interaction in biological molecules, particularly in natural enzymes that can affect their stability and activity . Inspiriting the important role of halogen bond in substrate selectivity of enzymatic catalysis, engineering the halogen interactions offer new and versatile tools for the rational design of supramolecular scaffolds in artificial enzymes technology.…”

Section: Figurementioning

confidence: 99%

Pt(II)‐Based Artificial Nitroreductase: An Efficient and Highly Stable Nanozyme

et al. 2019

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The nitroreductases are a family of natural enzymes with great importance. Inspired the integration of biology and nanotechnology, herein, a rational design for the preparation of the platinum(II)-based artificial nitroreductase is reported. Engineering the individual ligand scaffold, which on the one hand could form a highly stable complex with the platinum(II) as the catalytic active site and on the other hand could provide halogen bonding site for induce catalysis by approximation, creates an efficient and long-term resistance artificial nitroreductase. The platinum(II)-based artificial nitroreductase was characterized by FTIR, TEM, XRD, EDAX and ICP techniques. The reaction conditions were fully optimized for the reduction of high concentration p-nitrophenol as a specific substrate in aqueous solution employing experimental design, which highlights the potential application of the designed artificial nitroreductase in wastewater treatment. Moreover, the enzyme-like Michaelis-Menten kinetics of the reaction was investigated. The prepared platinum(II)-based artificial nitroreductase could be stable even after 20 catalytic cycles with excellent activity and it was represented a good turnover frequency.Nanomaterials with similar functions to those of proteins and their higher stability and lower cost are regarded as an important class of artificial enzymes known as "nanozymes". [1] Considering some practical limitations of natural enzymes, such as ease of denaturation, laborious preparation, high cost, and difficulty of recycling, the design and construction of efficient and stable nanozymes is highly desirable. [1b] The importance of nitroreductase enzymes to produce activate prodrugs, [2] remediate pollutants [3] and generate building-blocks for high-value pharmaceuticals [4] have attracted considerable attention of researchers in the artificial enzymes field. Moreover, various advanced nanocatalysts were developed for the reduction of 4nitrophenol based on immobilization of metal nanoparticles on different supporting materials such as metal-organic frameworks, [5] biohydrogels, [6] mesoporous silica materials [7] and core-shell magnetic materials. [8] In this regard and also as a part of our ongoing research program on the design of new nanocatalyst, [9] we have therefore constructed a rationally designed platinum(II)-based artificial nitroreductase for the reduction of 4-nitrophenol as a model substrate by sodium borohydride in aqueous solution.Halogen bonds are known as the highly directional and specific non-covalent interaction [10] in biological molecules, particularly in natural enzymes that can affect their stability and activity. [11] Inspiriting the important role of halogen bond in substrate selectivity of enzymatic catalysis, engineering the halogen interactions offer new and versatile tools for the rational design of supramolecular scaffolds [12] in artificial enzymes technology.The rational design of ligands lies at the heart of transitionmetal catalysis because of their critical roles in the...

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“…30 Our current knowledge regarding noncovalent interactions in halogenated molecules, and particularly of halogen bonds, is primarily based on computational and crystallographic studies of organic molecules and biomolecules. [31][32][33][34][35][36][37][38][39] Studies on the influence of halogen bonds in medicinal chemistry have also typically been performed by computational techniques.…”

Section: Introductionmentioning

confidence: 99%

The X40×10 Halogen Bonding Benchmark Revisited: Surprising Importance of (n–1)d Subvalence Correlation

et al. 2018

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We have re-evaluated the X40×10 benchmark for halogen bonding using conventional and explicitly correlated coupled cluster methods. For the aromatic dimers at small separation, improved CCSD(T)-MP2 "high-level corrections" (HLCs) cause substantial reductions in the dissociation energy. For the bromine and iodine species, (n-1)d subvalence correlation increases dissociation energies and turns out to be more important for noncovalent interactions than is generally realized; (n-1)sp subvalence correlation is much less important. The (n-1)d subvalence term is dominated by core-valence correlation; with the smaller cc-pVDZ-F12-PP and cc-pVTZ-F12-PP basis sets, basis set convergence for the core-core contribution becomes sufficiently erratic that it may compromise results overall. The two factors conspire to generate discrepancies of up to 0.9 kcal/mol (0.16 kcal/mol RMS) between the original X40×10 data and the present revision.

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The Important Role of Halogen Bond in Substrate Selectivity of Enzymatic Catalysis

Cited by 95 publications

References 42 publications

Looking Back, Looking Forward at Halogen Bonding in Drug Discovery

Looking Back, Looking Forward at Halogen Bonding in Drug Discovery

Pt(II)‐Based Artificial Nitroreductase: An Efficient and Highly Stable Nanozyme

The X40×10 Halogen Bonding Benchmark Revisited: Surprising Importance of (n–1)d Subvalence Correlation

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