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Chemical Structure| 1609-47-8 Chemical Structure| 1609-47-8
Chemical Structure| 1609-47-8

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CAS No.: 1609-47-8

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DEPC is used to inactivate RNase enzymes.

Synonyms: Diethyl pyrocarbonate

4.5 *For Research Use Only !

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Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

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Product Citations

Jonathan G. Kwok ;

Abstract: A long-standing goal in the field of chemical biology is coupling molecular recognition with the prowess of synthetic chemistry to produce novel compounds serving as chemical probes and therapeutic agents. One class of biomolecules that has gained considerable research focus and advancement for targeting is ribonucleic acid, RNA. Transcriptomic data have shown that both coding and non-coding RNA have critical roles in regulating every aspect of the central dogma of molecular biology. Although the research field continues to thrive in the development of RNA-binding ligands, current modalities are limited to targeting single-stranded and structurally complex RNA. The double-stranded RNA remains one of the most challenging structures to target. Double-stranded RNA is found in many functional tertiary and quaternary structured RNA and offers opportunities to modulate its biological activities. Herein, I describe my efforts for the design, synthesis, and biochemical and biophysical evaluations of a novel proteomimetic scaffold, referred to as the Crosslinked Helical Fork for the structure-and sequence-specific recognition of double-stranded RNA. Chapter 1 introduces the current advancements in targeting primary, secondary, and tertiary structured RNA. The topics for discussion will focus on modalities recognizing RNA in a sequence- or structured-specific manner and how current complex structured RNA are liganded. Chapter 2 describes the design and binding assessments of two ahelical RNA-binding peptides that mimic the groove-binding proteins Rnt1p from Saccharomyces cerevisiae and Tat from the equine infectious anemia virus. Chapter 3 addresses the issues from the results of Chapter 2 by introducing an encodable proteomimetic scaffold that mimics a dimeric a-helical RNA-binding viral protein binding in the major groove of double-stranded RNA. The synthetic scaffold was inspired by the Tomato Aspermy Virus 2b (TAV2b) protein. The chapter concludes with the firstgeneration design principles of targeting double-stranded RNA in a structure- and sequence-specific manner and future directions to improve the encodable scaffold. Additional supporting data can be found after Chapter 3 in the Appendix.

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Product Details of DEPC

CAS No. :1609-47-8
Formula : C6H10O5
M.W : 162.14
SMILES Code : O=C(OCC)OC(OCC)=O
Synonyms :
Diethyl pyrocarbonate
MDL No. :MFCD00009106
InChI Key :FFYPMLJYZAEMQB-UHFFFAOYSA-N
Pubchem ID :3051

Safety of DEPC

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

Application In Synthesis of DEPC

* 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.

  • Downstream synthetic route of [ 1609-47-8 ]

[ 1609-47-8 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 4065-45-6 ]
  • [ 1609-47-8 ]
  • [ 19337-04-3 ]
  • 2
  • [ 1609-47-8 ]
  • [ 56741-95-8 ]
  • [ 154379-07-4 ]
YieldReaction ConditionsOperation in experiment
17% With triethylamine; In DMF (N,N-dimethyl-formamide); at 65℃; for 20.0h; To a solution of 35 (0.25 g, 0.94 mmol) in DMF (8 mL) was added NEt3 (0.14 mL, 0.99 mmol) and diethyl pyrocarbonate (0.27 mL, 1.89 mmol). The reaction mixture was maintained at 65 C. for 20 h. The solvent was removed and the residue treated with DCM. The resulting mixture was filtered to remove the remaining starting material 35 and the filtrate washed with aqueous NaHCO3, brine and dried (MgSO4). The filtrate was concentrated and purified by HPLC (Thomson ODS-A 100A 5mu 150×21.2 mm column; flow rate=30 mL/min; CH3CN with 0.05% TFA (A), Water with 0.05% TFA (B); Make up pump flow=0.9 mL/min; Make up pump mobile phase; MeOH with 0.05% TFA using a gradient system as follows: t=0; 15% A, 85% B; t=3.0 min; 15% A, 85% B; t=9.5 min; 70% A, 30% B; t=10.0 min; 100% A, 0% B; t=12.0 min; 100% A, 0% B; t=12.5 min; 15% A, 85% B; t=15.0 min; 15% A, 85% B.) to afford 54 mgs of 36 (17%) as a clear oil: 1H NMR (400 MHz, CDCl3)delta 7.66 (m, 1H), 7.44 (m, 3H), 4.26 (q, J=7.6 Hz, 2H), 1.32 t, J=6.8 Hz, 3H); MS (+)-ES [M]+338.1 [M+2]+340.0 m/z. Elemental analysis for C13H12BrN3O3: calc'd: C, 46.17; H, 3.58; N, 12.43; found: C, 46.43; H, 3.74; N, 11.95.
  • 3
  • [ 22246-83-9 ]
  • [ 1609-47-8 ]
  • [ 340754-67-8 ]
YieldReaction ConditionsOperation in experiment
0.45 g (34%) With ammonium chloride; diisopropylamine; In tetrahydrofuran; n-heptane; dichloromethane; ethylbenzene; Method B An oven-dried flask was charged with <strong>[22246-83-9]8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one</strong> (0.976 g, 5.10 mmol) and anhydrous THF (30 mL). 1.9 M LDA in heptane/THF/ethylbenzene (5.90 mL, 11.24 mmol) was added dropwise via syringe at -78 C. under the protection of argon. The reaction mixture was allowed to warm up to room temperature, stirred for 1.5 hrs and cooled down to -78 C. again. A solution of diethyl pyrocarbonate (0.93 mL, 6.12 mmol) in anhydrous THF (5 mL) was added dropwise. After being stirred at -78 C. for 2 hrs and at room temperature for 1.5 hrs, the reaction mixture was quenched with saturated aqueous solution of NH4Cl (3 mL) and evaporated under reduced pressure. The residue was dissolved in dichloromethane, washed with water and dried over MgSO4. A purification of the crude product by flash chromatography on silica column with EtOAc/hexane (7:3) as an eluent provided 0.45 g (34%) of the desired compound as an oil that gradually crystallized at 0 C. over an extended period of time. M.P.=89-91 C. C14H18NO4 (264.29) MS (EI+) m/e 264 (M)+.
  • 4
  • [ 1609-47-8 ]
  • [ 405939-39-1 ]
  • [ 1355249-31-8 ]
YieldReaction ConditionsOperation in experiment
32% Example 15, Step F[00158] To LDA (177.21 mmol) in THF (100 mL) was added compound 15_2 (15 g, 53.7 mmol) in THF dropwise at 0C under N2 and the mixture stirred at 0C for 15 mins. Diethyl pyrocarbonate (28.73 g, 177.21 mmol) was then added dropwise at 0C and the reaction mixture stirred at room temperature overnight. The mixture was diluted with EtOAc and washed with water, brine, dried over MgS04and concentrated in vacuo. The residue was purified by silica column chromatography (PE: EtOAc=10:1 ) to afford product 15_3 (6 g, 32% yield).[00159] This compound was characterized by proton NMR (1HNMR) in accordance with the procedures described herein. Proton NMR yielded the following results: 1H NMR (CDC . 400 MHz): delta 9.409 (brs, 1 H), 4.367 (q, 2H, J=7.2 Hz), 1.577 (s, 9H), 1.380 (t, 3H, J=7.2 Hz).
32% Example 15, Step F[00158] To LDA (177.21 mmol) in THF (100 mL) was added compound 15_2 (15 g, 53.7 mmol) in THF dropwise at 0C under N2 and the mixture stirred at 0C for 15 mins. Diethyl pyrocarbonate (28.73 g, 177.21 mmol) was then added dropwise at 0C and the reaction mixture stirred at room temperature overnight. The mixture was diluted with EtOAc and washed with water, brine, dried over MgS04 and concentrated in vacuo. The residue was purified by silica column chromatography (PE: EtOAc=10:1) to afford product 15_3 (6 g, 32% yield).[00159] This compound was characterized by proton NMR (1HNMR) in accordance with the procedures described herein. Proton NMR yielded the following results: 1H NMR (CDCI3, 400 MHz): delta 9.409 (brs, 1 H), 4.367 (q, 2H, J=7.2 Hz), 1.577 (s, 9H), 1.380 (t, 3H, J=7.2 Hz).
  • 5
  • [ 5430-45-5 ]
  • [ 1609-47-8 ]
  • dimethyl diazomethylphosphonate [ No CAS ]
  • ethyl (R)-5-chloro-1-(diazo(dimethoxyphosphoryl)methyl)isoquinoline-2(1H)-carboxylate [ No CAS ]
  • 6
  • [ 623-73-4 ]
  • [ 5430-45-5 ]
  • [ 1609-47-8 ]
  • ethyl (R)-5-chloro-1-(1-diazo-2-ethoxy-2-oxoethyl)isoquinoline-2(1H)-carboxylate [ No CAS ]
 

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