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Chemical Structure| 288-13-1 Chemical Structure| 288-13-1
Chemical Structure| 288-13-1

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1H-pyrazole is an endogenous metabolite.

Synonyms: Pyrazole

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Product Citations

Product Citations

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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Product Details of 1H-pyrazole

CAS No. :288-13-1
Formula : C3H4N2
M.W : 68.08
SMILES Code : N1N=CC=C1
Synonyms :
Pyrazole
MDL No. :MFCD00005234
InChI Key :WTKZEGDFNFYCGP-UHFFFAOYSA-N
Pubchem ID :1048

Safety of 1H-pyrazole

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335-H412
Precautionary Statements:P261-P273-P305+P351+P338

Application In Synthesis of 1H-pyrazole

* 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.

  • Upstream synthesis route of [ 288-13-1 ]
  • Downstream synthetic route of [ 288-13-1 ]

[ 288-13-1 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 288-13-1 ]
  • [ 100-11-8 ]
  • [ 110525-57-0 ]
YieldReaction ConditionsOperation in experiment
76% With potassium carbonate In acetonitrile at 20℃; A mixture of 4-nitrobenzyl bromide (0.500 g, 2.31 mmol), lH-pyrazole (0.362 g, 5.23 mmol), and potassium carbonate (0.704 g, 5.09 mmol) in acetonitrile (30 mL) was stirred at rt overnight. After this time, the mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.380 g, 76percent) as a white solid. MW = 203.20. ]H NMR (CDC13, 500 MHz) δ 8.21-8.19 (m, 1H), 8.19-8.16 (m, 1H),7.61- 7.57 (m, 1H), 7.48-7.44 (m, 1H), 7.32-7.28 (m, 2H), 6.35 (t, / = 2.1 Hz, 1H), 5.44 (s, 2H); APCI MS m/z 204 [M + H]+.
References: [1] Organic Preparations and Procedures International, 2000, vol. 32, # 4, p. 385 - 390.
[2] Patent: WO2014/66659, 2014, A1, . Location in patent: Paragraph 0824.
  • 2
  • [ 288-13-1 ]
  • [ 100-14-1 ]
  • [ 110525-57-0 ]
References: [1] Tetrahedron Letters, 1986, vol. 27, # 51, p. 6209 - 6212.
[2] Farmaco, 1992, vol. 47, # 3, p. 335 - 344.
 

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