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Surveying the scope of aromatic decarboxylations catalyzed by prenylated-flavin dependent enzymes
Anushree Mondal ; Pronay Roy ; Jaclyn Carrannatto ; Prathamesh M. Datar ; Daniel J. DiRocco ; Katherine Huntera and E. Neil G. Marsh
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.
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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
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CAS No. : | 288-42-6 |
Formula : | C3H3NO |
M.W : | 69.06 |
SMILES Code : | O1C=NC=C1 |
MDL No. : | MFCD00009751 |
InChI Key : | ZCQWOFVYLHDMMC-UHFFFAOYSA-N |
Pubchem ID : | 9255 |
GHS Pictogram: | ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H225-H318 |
Precautionary Statements: | P210-P233-P280-P370+P378-P303+P361+P353-P305+P351+P338+P310 |
Class: | 3(8) |
UN#: | 2924 |
Packing Group: | Ⅱ |
* 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 |
---|---|---|
99% | [00443] To a solution of oxazole (4 g, 57.92 mmol) in THE (40 mL) -78 C under a nitrogen atmosphere was added dropwise n-BuLi (26 mL, 63.71 mmol). The reaction mixture was stirred for 15 min, ;.hen //-Bu SnCI (20 g, 61.81 mmol) was added slowly. The reaction mixture was stirred for 1 hour and then concentrated in vacuo to afford the title compound (20.7 g, 99%) as a deep pink oil which was used directly without further purification. NMR (400 MHz, CDCi): d 7.85 (s, 111), 7.19 (s, 111), 1.62 - 1.59 (m, Oi l). 1.37 - 1.32 (m, 1211), 0.93 - 0 90 (m, 9H). | |
77% | To a solution of oxazole (500 mg, 7.25 mmol) in THF (15 mL) at -78 C under N2 was added n-BuLi (2.5 M solution in hexanes, 2.9 mL, 7.32 mmol) dropwise and the mixture was stirred at -78 C for 30 min. Tributylchlorostannane (1.96 mL, 7.25 mmol) was then added and the mixture was allowed to warm to room temperature and stirred for 1 h. The solvent was removed under reduced pressure and residue was taken up in hexanes (50 mL). The resulting precipitate was removed by filtration and the filtrate was concentrated under reduced pressure to give the title compound I39 (2.0 g, 77%) as colourless oil. 1H NMR (400 MHz, DMSO-de) d 8.20 (s, 1H), 7.20 (s, 1H), 1.59 - 1.49 (m, 6H), 1.31 - 1.26 (m, 6H), 1.16 - 1.10 (m, 6H), 0.83 (t, J = 7.3 Hz, 9H). | |
77% | a) 2-(Tributylstannyl)oxazole I84 To a solution of oxazole (500 mg, 7.25 mmol) in THF (15 mL) at -78 C under N2 was added n-BuLi (2.5 M solution in hexanes, 2.9 mL, 7.32 mmol) dropwise and the mixture was stirred at -78 C for 30 min. Tributylchlorostannane (1.96 mL, 7.25 mmol) was then added and the mixture was allowed to warm to RT and stirred for 1 h. The solvent was removed under reduced pressure and residue was taken up in hexanes (50 mL). The resulting precipitate was removed by filtration and the filtrate was concentrated under reduced pressure to give the title compound (2.0 g, 77%) as colorless oil. NMR (400 MHz, DMSO -cfe) d 8.20 (s, 1H), 7.20 (s, 1H), 1.59 - 1.49 (m, 6H), 1.31 - 1.26 (m, 6H), 1.16 - 1.10 (m, 6H), 0.83 (t, J = 7.3 Hz, 9H). |
With n-butyllithium; In tetrahydrofuran; hexane; | A. 2-tributylstannyloxazole A solution of 1.00 g (14.5 mmol) of oxazole in 25 ml of THF at -78 C. was treated with 10.2 ml (14.6 mmol) of 1.43M butyllithium in hexane. After stirring for 30 minutes, an addition of 3.93 ml (14.5 mmol) of tributyltin chloride was made, and the solution was allowed to warm to room temperature. Stirring was continued for another hour after which most of the solvents were evaporated in vacuo. The resulting residue was taken up in 50 ml of hexane, and the resulting precipitate was separated by filtration through filtercel. Evaporation of the solvent from the filtrate provided 5.13 g of a colorless oil which was identified by NMR as the 2-stannyl derivative plus a small amount of tetrabutylstannane. | |
With n-butyllithium; In tetrahydrofuran; hexane; | A. 2 -tributylstannyloxazole A solution of 1.00 g (14.5 mmol) of oxazole in 25 ml of THF at -78 C. was treated with 10.2 ml (14.6 mmol) of 1.43M butyllithium in hexane. After stirring for 30 minutes, an addition of 3.93 ml (14.5 mmol) of tributyltin chloride was made, and the solution was allowed to warm to room temperature. Stirring was continued for another hour after which most of the solvents were evaporated in vacuo. The resulting residue was taken up in 50 ml of hexane, and the resulting precipitate was separated by filtration through filtercel. Evaporation of the solvent from the filtrate provided 5.13 g of a colorless oil which was identified by NMR as the 2-stannyl derivative plus a small amount of tetrabutylstannane. | |
To a cooled (-65oC) solution OF OXAZOLE (0.54 g) in THF (100 mL) is added drop-wise, a solution of 1.5 M nBuLi in pentane (5.7 mL) over a 5-minute period. The resulting solution is stirred for 35 minutes at-65oC at which time, a solution of tributyltin chloride (2.4 mL) in THF (10 mL) is added drop-wise, and the resulting solution is allowed to warm to 0oC. Several drops of water are added, and the solvent removed in vacuo to give 2- (TRIBUTYLSTANNYL)-1, 3-oxazole that is taken up in ET2O, washed with saturated KF, brine, dried (NA2S04), and concentrated to give an oil that is carried crude. | ||
Step H (2): Preparation of methyl 3-((i?)-2-(methoxymethyl)pyrrolidine- l-carbonyl)-5-(oxazol-2-yl)benzoate.; To a solution of oxazole (2.0 g, 29.0 mmol) in THF (30 mL) was added rø-butyl lithium (2.0 M solution in cyclohexanes, 16 mL, 31.9 mmol) at -780C slowly. The reaction mixture was stirred at -780C for 1.2 h, then tributylstannyl chloride (5.0 g, 15.4 mmol) was added. The reaction mixture was warmed up to rt over 3 h. Hexanes (200 mL) was added and the EPO <DP n="45"/>mixture was washed with H2O, dried over Na2SO4 and concentrated under vacuum to give 5.6 g of the 2-(tributylstannyl)oxazole ready for use. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6% | Oxazole (124 mg, 1.8 mmol) was dissolved in stirring tetrahydrofuran (20 mL) under nitrogen at -78° C. and treated with n-butyllithium (2.0 M in cyclohexane, 1.1 mL, 2.2 mmol) maintaining internal temperature below -60° C. After stirring ten minutes, ZnCl2 (0.48 g, 3.5 mmol) was added portionwise. The cooling bath was removed and the solution was allowed to reach room temperature. Tetrakis(triphenylphosphine)palladium(0) (30 mg, 5 mole percent) and <strong>[38696-20-7]5-bromo-2-phenylpyrimidine</strong> (309 mg, 1.30 mmol) were added and the mixture heated at 60° C. for four hours. Solvent was removed under reduced pressure and the mixture partitioned between saturated aqueous ammonium chloride and ethyl acetate. The organic phase was retained and additional ethyl acetate extractions of the aqueous phase performed. The combined extracts were dried with anhydrous sodium sulfate, the solution filtered, and solvent removed under reduced pressure. Purification by silica gel flash chromatography (9:1 to 7:3 v/v hexane-ethyl acetate) through a 12-g Silicycle.(R). flash silica cartridge afforded the title compound as an off-white solid (17 mg, 6percent yield); Rf 0.66 with 3:1 v/v hexane-ethyl acetate; melting point 175-177° C.; 1H-NMR (300 MHz; DMSO-d6) delta 9.42 (s, 2H), 8.48 (dd, 2H), 8.41 (s, 1H), 7.56-7.62 (m, 3H), 7.54 (s, 1H); MS (ESI+) m/z 224 (M+1), (ESI-) m/z 222 (M-1); H-PGDS FPBA IC50: 7.8 muM. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | With copper(l) iodide; palladium diacetate; In N,N-dimethyl-formamide; at 20 - 140℃; for 1.5h;Inert atmosphere; Sealed tube; Microwave irradiation; | General procedure: A 10 mL vial equipped with a small magnetic stirring bar wascharged with the appropriate bromo O-hetarene (1.0 equiv, 100mg), Pd(OAc)2 (5 mol%), and CuI (1.0 equiv). Anhyd DMF (1 mL)and the appropriate 1,3-azole (2.0 equiv) were added, and thevessel was purged with N2 and sealed with a PEEK snap cap. Themixture was stirred for 5 min at r.t. before the vessel was placedin the microwave reactor and the mixture was heated to 140 Cwith stirring for the appropriate time (usually 1 h). The solutionwas then cooled to r.t., diluted with EtOAc (15 mL), washed withsat. aq NH4Cl (2 × 15 mL) and dilute aq Na2S2O3 (10 mL). Theaqueous phases were extracted with EtOAc (2 × 10 mL), and theorganic phases were combined and washed with sat. aq NH4Cl(10 mL) and brine. Some H2O was added if any solids precipitatedduring the extraction. The combined organic phases weredried (MgSO4), filtered, and concentrated. The residue was purifiedby column chromatography (silica gel). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; nixantphos; In tetrahydrofuran; at 25℃; for 24h;Glovebox; Inert atmosphere; | General procedure: An oven-dried 10 mL reaction vial equipped with a stir bar was charged with azole heterocycles (1, 0.2 mmol, 1.0 equiv) and alkenyl bromides (2, 0.30 mmol, 1.5 equiv) in a glove box under a nitrogen atmosphere. A solution of catalytic Pd2(dba)3 (9.15 mg, 0.01 mmol, 5 mol%) and NiXantphos (11.03 mg, 0.02 mmol, 10 mol%) was stirred in 1 mL of dry tetrahydrofuran (THF) for 2 h at room temperature. Then, t-BuONa (57.7 mg, 0.6 mmol, 3.0 equiv) and reagent mixed with catalyst were added to the reaction mixture. And thenthe vial was capped. According to the temperature requirements for different products, some vials were stirred in the glove box for 24 h, but others were removed from the glove box, and stirred for 24 h at 70 or 150 . The reaction mixture was quenched with three drops of H2O, diluted with 3 mL of ethyl acetate, and filtered over a pad of silica. The pad was rinsed with ethyl acetate (15-25 mL), and the combined solutions were concentrated in vacuo. The crude material was loaded onto a deactivated silica gel column and purified by flash chromatography to afford the desired product. |
Tags: Oxazole | Oxazoles | Carboxylic Acids | Organic Building Blocks | Heterocyclic Building Blocks | 288-42-6
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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