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Surveying the scope of aromatic decarboxylations catalyzed by prenylated-flavin dependent enzymes
Anushree Mondal ; Pronay Roy ; Jaclyn Carrannatto , et al. Faraday Discuss.,2024,252,208-222. DOI: 10.1039/D4FD00006D PubMed ID: 38837123
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Abstract: The prenylated-flavin mononucleotide-dependent decarboxylases (also known as UbiD-like enzymes) are the most recently discovered family of decarboxylases. The modified flavin facilitates the decarboxylation of unsaturated carboxylic acids through a novel mechanism involving 1,3-dipolar cyclo-addition chemistry. UbiD-like enzymes have attracted considerable interest for biocatalysis applications due to their ability to catalyse (de)carboxylation reactions on a broad range of aromatic substrates at otherwise unreactive carbon centres. There are now ∼35[thin space (1/6-em)]000 protein sequences annotated as hypothetical UbiD-like enzymes. Sequence similarity network analyses of the UbiD protein family suggests that there are likely dozens of distinct decarboxylase enzymes represented within this family. Furthermore, many of the enzymes so far characterized can decarboxylate a broad range of substrates. Here we describe a strategy to identify potential substrates of UbiD-like enzymes based on detecting enzyme-catalysed solvent deuterium exchange into potential substrates. Using ferulic acid decarboxylase (FDC) as a model system, we tested a diverse range of aromatic and heterocyclic molecules for their ability to undergo enzyme-catalysed H/D exchange in deuterated buffer. We found that FDC catalyses H/D exchange, albeit at generally very low levels, into a wide range of small, aromatic molecules that have little resemblance to its physiological substrate. In contrast, the sub-set of aromatic carboxylic acids that are substrates for FDC-catalysed decarboxylation is much smaller. We discuss the implications of these findings for screening uncharacterized UbiD-like enzymes for novel (de)carboxylase activity.
Purchased from AmBeed: 27916-43-4 ; 2438-05-3 ; 501-89-3 ; 42287-94-5 ; 776-79-4 ; 53473-36-2 ; 7251-61-8 ; 42287-97-8 ; 1621-91-6 ; 37718-11-9 ; 288-13-1 ; 86-73-7 ; 104-53-0 ; 2018-90-8 ; 87-66-1 ; 135-19-3 ; 1664-57-9 ; 289-80-5 ; 693-95-8 ; 55-22-1 ; 102-93-2 ; 1477-50-5 ; 1632-76-4 ; 4780-79-4 ; 16642-79-8 ; 3581-89-3 ; 501-97-3 ; 771-50-6 ; 98-98-6 ; 619-64-7 ; 100-51-6 ; 402-45-9 ; 59-67-6 ; 93-60-7 ; 273-53-0 ; 2084-13-1 ; 51-17-2 ; 2459-09-8 ; 2459-07-6 ; 95-16-9 ; 459-31-4 ; 90-05-1 ; 150-76-5 ; 103-25-3 ; 271-44-3 ; 6293-56-7 ; 2550-26-7 ; 288-32-4 ; 501-52-0 ; 2001-32-3 ; 1592-38-7 ; 95-15-8 ; 91-19-0 ; 1122-61-8 ; 3724-19-4 ; 20173-24-4 ; 118-31-0 ; 6125-24-2 ; 60-12-8 ; 90-15-3 ; 120-72-9 ; 822-36-6 ; 288-47-1 ; 288-42-6 ; 2038-57-5 ; 38628-51-2 ; 1929-29-9 ; 15009-91-3 ; 1505-50-6 ; 581-40-8 ; 616-47-7 ; 1571-33-1 ...More
CAS No. : | 402-45-9 | MDL No. : | MFCD00002363 |
Formula : | C7H5F3O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BAYGVMXZJBFEMB-UHFFFAOYSA-N |
M.W : | 162.11 | Pubchem ID : | 67874 |
Synonyms : |
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Signal Word: | Danger | Class: | 4.1,6.1 |
Precautionary Statements: | P210-P240-P241-P261-P264-P270-P271-P280-P301+P310+P330-P302+P352-P304+P340+P312-P305+P351+P338+P310-P332+P313-P370+P378-P403+P233-P405-P501 | UN#: | 2926 |
Hazard Statements: | H228-H301-H315-H318-H335 | Packing Group: | Ⅱ |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; at 0 - 20℃; | 2- (4-TRIFLUOROMETHYI-PHENOXYMETHYL)-PROP-2-EN-1-OL; To a mixture of 4-TRIFLUOROMETHYLPHENOL (49.0 g, 302 mmol), 2-methylene- 1, 3-PROPANEDIOL (40.0 g, 454 MMOL), and diisopropyl azodicarboxylate (67.4 g, 333 MMOL) in CH2C12 (400 mL) at 0°C was charged with a solution of TRIPHENYLPHOSPHINE (87.2 g, 333 MMOL) in CH2Cl2 (400 mL) dropwise. After the mixture was stirred at 0°C and then allowed to warm up to room temperature overnight, CH2C12 was evaporated under reduced pressure. To the residue was added ET20 and hexane, and the mixture was cooled to 0°C. The precipitated solid was filtered, and the filtrate was concentrated and column chromatographed (EtOAc/hexane: 1/4) to give 35.2 g (50percent) of 2-A ;'H NMR (300 MHz, CDCl3) 8 7.55 (d, J = 8. 6 HZ, 2 H), 6.99 (d, J = 8. 6 HZ, 2 H), 5.33 (d, J = 0. 9 HZ, 1 H), 5.29 (d, J = 0. 9 Hz, 1 H), 4.65 (s, 2 H), 4.27 (d, J = 6. 0 Hz, 2 H). |
50% | With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; at 0 - 20℃; | 2-(4-Trifluoromethyl-phenoxymethyl)-prop-2-en-1-ol To a mixture of 4-trifluoromethylphenol (49.0 g, 302 mmol), <strong>[3513-81-3]2-methylene-1,3-propanediol</strong> (40.0 g, 454 mmol), and diisopropyl azodicarboxylate (67.4 g, 333 mmol) in CH2Cl2 (400 mL) at 0° C. was charged with a solution of triphenylphosphine (87.2 g, 333 mmol) in CH2Cl2 (400 mL) dropwise. After the mixture was stirred at 0° C. and then allowed to warm up to room temperature overnight, CH2Cl2 was evaporated under reduced pressure. To the residue was added Et2O and hexane, and the mixture was cooled to 0° C. The precipitated solid was filtered, and the filtrate was concentrated and column chromatographed (EtOAc/hexane: 1/4) to give 35.2 g (50percent) of 2-A; 1H NMR (300 MHz, CDCl3) delta 7.55 (d, J=8.6 Hz, 2 H), 6.99 (d, J=8.6 Hz, 2 H), 5.33 (d, J=0.9 Hz, 1 H), 5.29 (d, J=0.9 Hz, 1 H), 4.65 (s, 2 H), 4.27 (d, J=6.0 Hz, 2 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Step 3[00247] To a solution of triphenylphosphine (3 eq) in dry THF under Argon was added diethylazodicarboxylate (3 eq) dropwise. The reaction mixture was stirred at room temperature for 15 minutes before adding a solution of 4-(trifluoromethyl)phenol (3eq in dry THF) dropwise. The reaction mixture was stirred at room temperature for 1 hour before adding (R)-methyl 3-hydroxy-2-(tritylamino)propanoate (LXXXIX) in dry THF in one portion. The reaction mixture was stirred at room temperature ovenight. The mixture was concentrated to dryness, treated with hexane and filtered. The residue was concentrated to dryness and purified by silica flash chromatography (EtOAc/hexane = 1 :5). Pure (R)-methyl 3-(4- (trifluoromethyl)phenoxy)-2-(tritylamino)propanoate (XC) was obtained as an off-white solid (50% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 0 - 20℃; for 16h;Inert atmosphere; | Preparation of intermediate BP DIAD ( 1.40 g, 6.92 mmol) in toluene ( 10 mL) was added to a solution of tert-butyl 6-hydroxy-2-azaspiro[3.3]lieptane-2-carboxyl.ate (CAS [1147557-97-8], 1.2 g, 5.63 mmol), 4-(trifluoromethyl)phenol (CAS [402-45-9], 1.10 g, 6.75 mmol), and triphenylphosphine (2.31 g, 8.80 mmol) in toluene (40 mL) at 0 °C under N2 flow. The mixture was stirred overnight at room temperature. The mixture was concentrated. The crude product was purified by column chromatography over silica gel (petroleum ether/ethyl acetate from 1/0 to 3/1). The desired fraction was collected and concentrated to give intermediate BP, 2 g, 99percent. |
With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 0 - 20℃; for 16h;Inert atmosphere; | DIAD ( l .40 g, 6.92 mmol) in toluene ( 10 mL) was added to a solution of tert-butyl (0207) 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxyl.ate (CAS [1147557-97-8], 1.2 g, (0208) 5.63 mmol), 4-(trifluoromethyl)phenol (CAS [402-45-9], 1.10 g, 6.75 mmol), and (0209) triphenylphosphine (2.31 g, 8.80 mmol) in toluene (40 mL) at 0 °C under N2 flow. The mixture was stirred overnight at room temperature. The mixture was concentrated. The crude product was purified by column chromatography over silica gel (petroleum (0210) ether/ethyl acetate from 1/0 to 3/1). The desired fraction was collected and concentrated to give intermediate E, 2 g, 99percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium carbonate; In dimethyl sulfoxide; at 110℃; for 1h; | 2-Cyano-5-fluoropyridine (3.54 g; 28.99 mmol), 4-trifluoromethyl-phenol (4.70 g; 28.99 mmol) and potassium carbonate (6.01 g; 43.49 mmol) are stirred in DMSO (150 mL) at 1 10C for 1 hour. The reaction mixture is diluted with water and extracted with EtOAc. The organic layer is washed with water, separated, dried over Na2S04, filtered and concentrated under reduced pressure. (1126) Yield: quantitative ESI-MS: m/z = 265 [M+H]+ Rt(HPLC): 1 .03 min (method 10) |
92% | With potassium carbonate; In N,N-dimethyl acetamide; at 100℃; for 6h; | Step A: A mixture of 4-(trifluoromethyl)phenol (2.9 g,18 mmol), <strong>[327056-62-2]2-cyano-5-fluoropyridine</strong> (2.0 g, 9.0 mmol), K2CO3(2.7 g, 20 mmol) and DMA (20 mL) was stirred at 100 C for 6 h.After cooling to room temperature, the reaction mixture wasdiluted with water and extracted with AcOEt. The organic layerwas washed with brine, dried over Na2SO4 and concentrated invacuo. The resulting residue was purified by silica gel chromatography(hexane-AcOEt) to give 5-[4-(trifluoromethyl)phenoxy]pyridine-2-carbonitrile (4.0 g, 92%) as a colorless solid. 1H NMR (CDCl3)d: 8.50 (1H, d, J = 2.4 Hz), 7.71-7.69 (3H, m), 7.35 (1H, dd, J = 8.8,2.9 Hz), 7.19 (2H, d, J = 8.8 Hz). MS (ESI+) m/z: 264 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With caesium carbonate; In N,N-dimethyl-formamide; at 120℃; for 0.5h; | ComuMercially available <strong>[124467-36-3]2-chloro-7,8-dihydroquinolin-5(6H)-one</strong> (0.20 g, 1.10 muMol) was dissolved in DMF (5.5mL), and cesium carbonate (0.72 g, 2.20 muMol) and 4-(trifluoromethyl)phenol (0.72 g, 1.65 muMol) were added to thesolution. The mixture was subjected to a reaction at a temperature of 120C for 30 minutes using a microwave reactormanufactured by Biotage. Water was added to the mixture. The organic layer was extracted with ethyl acetate, washedwith saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residuewas purified by silica gel column chromatography (heptane/ethyl acetate = 90/10 -> 60/40) to obtain compound 103-1(0.23 g, 68%).1H NMR (400 MHz, CDCl3, delta): 8.32 (d, J = 8.6 Hz, 1H), 7.68 (d, J = 8.6 Hz, 2H), 7.29 (d, J = 8.6 Hz, 2H), 6.85 (d, J =8.6 Hz, 1H), 2.96 (t, J = 6.1 Hz, 2H), 2.65 (t, J = 6.6 Hz, 2H), 2.15 (tt, J = 6.6, 6.1 Hz, 2H).ESIMS m/z: [M + H]+ 308. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 21h; | Combine (R)-3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (1.00g, 5.34mmol), 4-(trifluoromethyl)phenol (865mg, 5.34mmol), PPh3 (2.00g, 5.83mmol) Add THF (20mL), transfer to 0C, slowly add DIAD (1.40mL, 7.11mmol), after the addition, transfer the reaction to room temperature for 21h. The reaction solution was concentrated under reduced pressure. The concentrated solution was diluted with methyl tert-butyl ether (30 mL) and stirred at -20C. A large amount of white insoluble solids precipitated. Filtered while cold, and washed the filter cake with cold methyl tert-butyl ether The filtrate was concentrated under reduced pressure, and the concentrated solution was separated by silica gel column chromatography (eluent: PE/EtOAc (v/v)=6/1) to obtain a pale yellow liquid (1.76 g, 100%). |
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