Metallocavitins as Advanced Enzyme Mimics and Promising Chemical Catalysts
Abstract
:1. Introduction
2. The Diversity of Cavitins
2.1. Metallocavitins
2.2. Design and Characterization
3. Cavity Effects
3.1. Isolation from Bulky Solvent, Selective Incorporation and Stabilization of the M-Complex and Reactants
3.2. Preorganization of the M-Catalyst and Reagents, Mutual Orientation and Sha** the Reaction Start Complex
3.3. Transition State and Intermediate Stabilization
3.4. Second Sphere and Allosteric Effects
3.5. Changing the Reaction Course and Mechanism
3.6. Regioselectivity, Stereoselectivity and Product Selectivity
4. M-Cavitins as Advanced Chemical Models of Enzymes
4.1. Stereoselectivity
4.2. Artificial Photosynthesis
4.3. Models of Redox-Active Enzymes
4.4. MMO Mimics
5. M-Cavitins in Fine Organic Synthesis
6. M-Cavitins as Promising Industrial Catalysts
6.1. H2O
6.2. CO2
6.3. Methane
7. Conclusions and Outlooks
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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# | MC | Reaction + hν | Productivity, μmol g−1 (Time, h−1) | Select. % | Rate, μmol g−1h−1 (TOF, h−1) | References |
---|---|---|---|---|---|---|
1 | FDH@Rh-NU-1000 | CO2 + 2e2H+ HCOOH | 144 M (24) | nd | (865) | [91] |
2 | UiO67-Ir-Cou6 | CO2 H2 HCOOH | 26,845 4808 | 95.5 | nd | [92] |
3 | MIL-125-Py-Rh | CO2 HCOOH | 9.5 mM (24) | nd | nd | [93] |
4 | CUST-804 | CO2 CO | nd | 82.8 | 2,710 | [94] |
5 | Rh-MOP | CO2 HCOOH | 76 | nd | (60) | [95] |
6 | MAF-34-CoRu | CO2 + H2O CO | nd | nd | 11.2 | [96] |
7 | PFC-58-30 | CO2 + H2O HCOOH | nd | nd | 29.8 | [97] |
8 | POMs@INEP-20 | CO2 → CO | nd | 97.1 | 970 (2.43) | [98] |
9 | CABB@M-Ti | CO2 → CH4 | nd | 88.7 | 32.9 | [99] |
10 | CTF-Bpy-Co | CO2 → CO | 120 μmol (10) | 83.8 | nd | [100] |
11 | SAS/Tr-COF | CO2 → CO | 96.4 | 980.3 | [101] | |
12 | RuCOF-TPB | H2O → H2 | 160 | nd | 20,308 | [102] |
13 | CoP@ZnIn2S4 | H2O → H2 | nd | nd | 103 | [103] |
14 | ZIF-67/CdS HS | H2O → H2 | nd | nd | 1721 | [104] |
15 | Ni-Py-COF | H2O → H2 | nd | nd | 626 | [105] |
16 | Co-Tz | H2O → H2 | 9,320 | nd | 2,330 | [106] |
17 | PTC-318 | H2O → H2 | 80 | nd | nd | [107] |
18 | Ru(Bda)-COF | H2O → O2 | nd | nd | 26,000 | [108] |
# | MC | Enzyme | Reaction | Yield, % (µmol g−1) | Select, % | Rate, µmolg−1 h−1 (TOF, h−1) | Refs |
---|---|---|---|---|---|---|---|
1 | Cu3MOF-818 | Catechol oxidase | DTBC + O2 → DTBQ + H2O2 | 98 | nd | nd | [111] |
2 | Cu2MIL-125-Ti | Mono oxygenase | RH + O2 ROH epoxide | 94 92 | nd | nd | [112] |
3 | Ce-AQ MOF | Mono oxygenase | C6H12 +O2 C6H10O | 54.2 | 98.4 | nd | [113] |
4 | Ce-UiO-Co | MMO | CH4 +H2O2 CH3OH + H2O | (2,166,000) | 99 | nd | [114] |
5 | Fe/Co-TFT | Hydrogenase | 2H+ + 2e− ⇄ H2 | nd | nd | (11,000) | [115] |
6 | UiO-MOF-Fe2S2 | Hydrogenase | 2H+ + 2e− ⇄ H2 | 35 | nd | nd | [116] |
7 | [Pd12(Fe2BB)5 (BBNH+)19]43+ | Hydrogenase | 2H+ + 2e− ⇄ H2 | nd | nd | 10,300 mol−1s−1 | [117] |
8 | Mg3(HiTP)2 | Reductase | O2 + 2e,2H+ → H2O2 | nd | 90 | nd | [118] |
9 | UiO66(SH)2 | Nitrogenase | N2 + 6e,6H+ → 2NH3 | nd | nd | 32.4 | [119] |
10 | NFCO | Nitrogenase | N2 + 6e,6H+ → 2NH3 | 17,600 | nd | 126 | [120] |
11 | MIL-101 (FeII/FeIII) | Nitrogenase | N2 + 6e,6H+ → 2NH3 | nd | nd | 466.8 | [121] |
# | MC | Reaction | Yield, % | Selectivity, % | Rate, mmol g−1h−1 (TOF, h−1) | References |
---|---|---|---|---|---|---|
1 | PdNPs/ZIF-8 | PhNO2 + H2 → PhNH2 | 95 | nd | nd | [140] |
2 | (Cu1Pd1)PCN-22(Co) | 2PhY + CO2 → Ph2CO | 90 | 97 | nd | [141] |
3 | Br-PMOF(Ir) | PhEtNH + CO2 + PhSiH2 → PhEtNCHO | 82 | 82 | (507) | [142] |
4 | Zn-TACPA | XC6H4NHCHCOOEt + PhCH=CH2 → 3a [143] | 91 | nd | nd | [143] |
5 | Co@Y | MeCH=CH2 + O2 → epoxyde | 24.6 | 57 | 4.7 | [144] |
6 | CoP@POC | 2PhCH2NH2 + O2 → PhCH2N=CHPh | 93 | 99 | (22,989) | [145] |
7 | CuHENU-8 | Me2PhSiH + t-BuOOH → Me2PhSiOH | 89 | 95 | 132 | [146] |
8 | Ni-SAPO-34 | C6H10=O + O2 → C4H10(COOH)2 | 30 | 87 | nd | [147] |
9 | Prism1 | ArCH2OH + O2 → ArCHO | 99.9 | nd | nd | [148] |
10 | POM/MOF | PhCH=CH2 + H2O2 → PhCHO | 96 | 99 | nd | [149] |
11 | Zr-abtc | Carvone + H2O2 → 1,2-epoxide | 87 | 90 | nd | [150] |
12 | SNNU-97-InV | Me-epoxide + CO2 → Me-c-carbonate | 73.3 | 99 | (24.2) | [151] |
13 | NUC-45a | Ph-epoxide + CO2 → Ph-carbonate | 99 | 99 | (316) | [152] |
14 | NUC-54a | PhCHO + CO2 → Ph-carbonate | 98 | nd | (47) | [153] |
15 | MOF1 | 1-Et-2Ph-aziridine + CO2 → oxazolidinone | 99 | 97 | nd | [139] |
16 | Ent-1(3b) | nerol → α-terpineol +limonen | 73 | 70ee | nd | [154] |
17 | CuPMO | NH2C6H4OH + CH2(COMe)2 → benzoazole | 83 | nd | nd | [155] |
18 | Ni-Ir@Tp-Bpy | R1R2NH + RJ → R1R2NR | 94 | nd | nd | [156] |
19 | Cu2O@ZIF-8 | Me2C(OH)-C≡CH + CO2 → α-alkylidenecarbonate | 97 | nd | (3.03) | [157] |
20 | (R)-CuTAPBP-COF | EtCHO+PyCH2Br (R)-MPP | 98 | 95ee | nd | [158] |
21 | JLU-MOF-112 | PhCHO + CH2(CN)2 → PhCH=C(CN)2 | 98 | nd | (198) | [159] |
22 | Cu-1D MOF | Pyrazole + PhJ → 1-Ph-1H-pyrazole | 95 | nd | nd | [160] |
23 | PdAg@ZIF-8 | CH2=CHC6H4NO2 + H2 → CH2=CHC6H4NH2 | 98 | 97.5 | nd | [161] |
24 | JNM-4-Ns | R1C6H4-C≡CR2 + B2Pin2 → R1C6H4-CH=CR2BPin | 90 | nd | (41,734) | [162] |
25 | UiO-66-Gua0.2 | CO2 + ECH → CPC | nd | nd | (110.3) | [163] |
26 | Bi2S3@quasi-Bi-MOF | 4-NO2PhOH + H2 → 4-NH2PhOH | nd | 97 | nd | [164] |
# | MC | Reaction | Yield, % (P, µmol g−1/FE, %) | Selectivity, % | Rate, µmol g−1h−1 (TOF h−1) | OP, mV (CD, mA sm−2) | Refs |
---|---|---|---|---|---|---|---|
1 | Fe/Ni-MOF | H2O → O2 | nd | nd | (940) | 239 (50) | [166] |
2 | CALF20 | CO2 → CO | (nd/94) | nd | (1361) | (32.8) | [167] |
3 | HNTM-Ir/Pt | H2O → H2 | (600) | nd | 201.9 | nd | [168] |
4 | IrIII-Uio-67-NH2 | CO2 → CO | nd (nd/6.71) | 99.5 | (120) | nd | [75] |
5 | TiO2@ZIF-8 | H2O → H2 | 51 1 | nd | 262,000 | nd | [18] |
6 | (NiCo)S2/NCNF | H2O → O2 → H2 | nd | nd | nd | 177 (10) 203 (10) | [169] |
7 | ZnO/Fe2O3 PN | CH4 → CH3OH | (178.3/nd) | 100 | nd | nd | [170] |
8 | Mn1Co1/CN | CO2 → CO | nd | nd | 47 | nd | [171] |
9 | ZPMOF | CO2 → CH4 | nd | 70 | 32 | nd | [172] |
10 | T1-2Cu | CO2 → CH4 | nd | 93 | 3.7 | nd | [173] |
11 | NiFe-MOF/FF | H2O → O2 | nd | 83.8 | nd | 216 (50) | [174] |
12 | Cu@FCN MOF/CF | H2O → O2 | nd | 88.7 | nd | 290 (10) | [175] |
13 | Fe3-MOF-BDC-NH2 | H2O → O2 | nd | nd | nd | 280 (10) | [176] |
14 | CoCu-MOF NBs | H2O → O2 | nd | nd | 1084 | 271 (10) | [177] |
15 | CuNi-NKU-101 | H2O → H2 | nd | 100 | nd | 324 (10) | [178] |
16 | SnTPPCOP | H2O → H2 | nd | nd | nd | 147 (10) | [179] |
17 | CoP/CNTHPs | H2O → O2 → H2 | nd | nd | nd | 238 (10) 147 (10) | [180] |
18 | Ru/3DMNC | H2O → O2 → H2 | nd | nd | nd | 217 (10) 51 (10) | [181] |
19 | MnZn-MUM-1/NF | H2O → O2 | nd | nd | (83.3) | 253 (10) | [182] |
20 | Co-Fe-P | H2O → O2 | nd | nd | nd | 240 (10) | [183] |
21 | Ce-Ni(OH)2 @Ni-MOF | H2O → O2 | nd | nd | (170) | 272 (100) | [184] |
22 | FePc-pz | N2 → NH3 | (nd/31.9) | nd | 33.6 2 | nd | [185] |
23 | Fe1Sx@TiO2 | N2 → NH3 | (nd/17.3) | nd | 18.3 2 | nd | [186] |
24 | UiO-66-H | CH4 → CH3OOH | nd | 100 | 350 | nd | [187] |
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Shteinman, A.A. Metallocavitins as Advanced Enzyme Mimics and Promising Chemical Catalysts. Catalysts 2023, 13, 415. https://doi.org/10.3390/catal13020415
Shteinman AA. Metallocavitins as Advanced Enzyme Mimics and Promising Chemical Catalysts. Catalysts. 2023; 13(2):415. https://doi.org/10.3390/catal13020415
Chicago/Turabian StyleShteinman, Albert A. 2023. "Metallocavitins as Advanced Enzyme Mimics and Promising Chemical Catalysts" Catalysts 13, no. 2: 415. https://doi.org/10.3390/catal13020415