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Revision as of 12:17, 17 February 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL KEGG.← Previous edit		Latest revision as of 13:27, 21 November 2024 edit undoDMacks (talk | contribs)Edit filter managers, Autopatrolled, Administrators186,428 edits Removing from Category:Carbonate esters using Cat-a-lot
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	{{Orphan|date=February 2009}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 396341815		| verifiedrevid = 443637574
	| ImageFile = Diethyl pyrocarbonate.svg		| ImageFile = Diethyl pyrocarbonate.svg
	| ImageSize = 250px		| ImageSize =
	| ImageFile2 = Diethyl pyrocarbonate3d.png		| ImageFile2 = Diethyl pyrocarbonate3d.png
	| ImageSize2 = 250px		| ImageSize2 =
	| IUPACName = diethyl dicarbonate		| PIN = Diethyl dicarbonate
			| OtherNames = {{bulletedlist|Diethylpyrocarbonate|Diethyl oxydiformate|Ethoxyformic anhydride|Pyrocarbonic acid diethyl ester|DEPC}}
	| OtherNames =
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 2943		| ChemSpiderID = 2943
			| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C11592		| KEGG = C11592
	| InChI = 1/C6H10O5/c1-3-9-5(7)11-6(8)10-4-2/h3-4H2,1-2H3		| InChI = 1/C6H10O5/c1-3-9-5(7)11-6(8)10-4-2/h3-4H2,1-2H3
	| InChIKey = FFYPMLJYZAEMQB-UHFFFAOYAU		| InChIKey = FFYPMLJYZAEMQB-UHFFFAOYAU
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 55517		| ChEMBL = 55517
			| EC_number = 216-542-8
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C6H10O5/c1-3-9-5(7)11-6(8)10-4-2/h3-4H2,1-2H3		| StdInChI = 1S/C6H10O5/c1-3-9-5(7)11-6(8)10-4-2/h3-4H2,1-2H3
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = FFYPMLJYZAEMQB-UHFFFAOYSA-N		| StdInChIKey = FFYPMLJYZAEMQB-UHFFFAOYSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 1609-47-8		| CASNo = 1609-47-8
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| PubChem = 3051
			| UNII = LMR3LZG146
⚫	| SMILES = O=C(OCC)OC(=O)OCC
		⚫	| PubChem = 3051
⚫	| MeSHName = Diethylpyrocarbonate
			| ChEBI_Ref = {{ebicite|correct|EBI}}
			| ChEBI = 59051
		⚫	| SMILES = O=C(OCC)OC(=O)OCC
		⚫	| MeSHName = Diethylpyrocarbonate
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
			| C=6 | H=10 | O=5
	| Formula = C<sub>6</sub>H<sub>10</sub>O<sub>5</sub>
			| Appearance = Clear, colorless liquid
	| MolarMass = 162.141 g/mol
			| Density = 1.101 g/mL at 25 °C<br />1.121 g/mL at 20 °C
	| Appearance =
	| Density =		| MeltingPt =
			| BoilingPtC = 93 to 94
	| MeltingPt =
			| BoilingPt_notes = at 24 hPa
	| BoilingPt =
	}}		}}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
	| Solubility =		| MainHazards = Harmful
	| MainHazards =		| FlashPtC = 69
			| FlashPt_notes = closed cup
	| FlashPt =
	| Autoignition =		| AutoignitionPt =
			| LD50 = Oral - rat - 850 mg/kg
			| GHSPictograms = {{GHS07}}
			| GHSSignalWord = Warning
			| HPhrases = {{H-phrases|302|315|319|332|335}}
			| PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+312|304+340|305+351+338|312|321|330|332+313|337+313|362|403+233|405|501}}
			}}
			|Section8={{Chembox Related
			| OtherCompounds = ]<br />]
	}}		}}
	}}		}}
	'''Diethylpyrocarbonate''' (DEPC), also called diethyl dicarbonate (] name), diethyl oxydiformate, ethoxyformic anhydride, or pyrocarbonic acid diethyl ester, is used in the ] to inactivate the ] ] from water and other laboratory utensils. It inactivates the RNases by the ]s of the ] residues. DEPC cannot be used with ] buffer or ] since they inactivate DEPC by reacting with it. In contrast it can be used with PBS or ]. A handy rule is that enzymes or chemicals which have active -O:, -N: or -S: cannot be treated with DEPC to become RNase-free as DEPC reacts with these species. Furthermore DEPC degradation products can inhibit ].
			'''Diethyl pyrocarbonate''' ('''DEPC'''), also called '''diethyl dicarbonate''' (] name), is used in the ] to inactivate ] ]s in water and on laboratory utensils. It does so by the ] modification of ] (most strongly), ], ], and ] residues.<ref>{{cite journal|author=Chirgwin, John M|year=1979|title=Isolation of biologically active ribonucleic acid from sourcesenriched in ribonuclease|journal=Biochemistry|volume=18|issue=24|pages=5294–5299|doi=10.1021/bi00591a005|pmid=518835|display-authors=etal}}</ref><ref>{{cite journal|doi=10.1111/j.1432-1033.1970.tb00955.x|title=A Mechanism of the Irreversible Inactivation of Bovine Pancreatic Ribonuclease by Diethylpyrocarbonate. A General Reaction of Diethylpyrocarbonate with Proteins|year=1970|last1=Wolf|first1=Barry|last2=Lesnaw|first2=Judith A.|last3=Reichmann|first3=Manfred E.|journal=European Journal of Biochemistry|volume=13|issue=3|pages=519–25|pmid=5444158|doi-access=free}}</ref>
⚫	Water is usually treated with 0.1% v/v diethylpyrocarbonate for at least 1 hour at 37°C and then autoclaved (at least 15 min) to inactivate traces of DEPC. Inactivation of DEPC in this manner yields CO<sub>2</sub>, H<sub>2</sub>O and EtOH. Higher concentrations of DEPC are competent of deactivating larger amounts of RNAse but remaining traces or byproducts may inhibit further biochemical reactions such as in vitro translation. Further on, chemical modification of RNA such as carboxymethylation is possible when traces of DEPC or its byproducts are present, resulting to reduced usage of RNA even after buffer exchange (after precipitation).
		⚫	DEPC-treated (and therefore RNase-free) water is used in handling of ] in the laboratory to reduce the risk of RNA being degraded by RNases.
		⚫	Water is usually treated with 0.1% v/v DEPC for at least 2 hours at 37&nbsp;°C and then ]d (at least 15 min) to inactivate traces of DEPC. Inactivation of DEPC in this manner yields CO<sub>2</sub> and ]. Higher concentrations of DEPC are capable of deactivating larger amounts of RNase, but remaining traces or byproducts may inhibit further biochemical reactions such as in vitro transcription. Furthermore, chemical modification of RNA such as carboxymethylation is possible when traces of DEPC or its byproducts are present, resulting in impaired recovery of intact RNA even after buffer exchange (after precipitation).
	]		]
⚫	DEPC treated (and therefore RNase-free) water is used in handling of RNA in the laboratory, to reduce the risk of RNA being degraded by RNases.
			DEPC is unstable in water and susceptible to hydrolysis to carbon dioxide and ethanol, especially in the presence of a ]. For this reason, DEPC cannot be used with ] or ] buffers. In contrast, it can be used with ] or ].<ref name=sigma>{{cite web|title=FAQ about DEPC|url=http://sigma-aldrich.custhelp.com/app/answers/detail/a_id/268/p/7,117/session/L3RpbWUvMTM0NDc1NzUxNC9zaWQvbzh6M3d1M2w%3D|publisher=Sigma-Aldrich|accessdate=12 August 2012}}</ref> A handy rule is that enzymes or chemicals which have active -O:, -N: or -S: cannot be treated with DEPC to become RNase-free, as DEPC reacts with these species. Furthermore, DEPC degradation products can inhibit in vitro transcription.
⚫	DEPC derivatization of histidines is also used to study the importance of histidyl residues in enzymes. Modification of ] by DEPC results in carbethoxylate derivates at the N-omega-2 nitrogen of the ] ring. DEPC modification of histidines can be reversed by treatment with 0.5M ] at neutral pH.
		⚫	DEPC ] of histidines is also used to study the importance of histidyl residues in enzymes. Modification of ] by DEPC results in carbethoxylated derivates at the N-omega-2 nitrogen of the ] ring. DEPC modification of histidines can be reversed by treatment with 0.5 M ] at neutral pH.
⚫	== External links ==
⚫	*
⚫	*
			DEPC can also be used for probing the structure of double-stranded DNA.{{citation needed|date=March 2021}}
			==See also==
	{{biochem-stub}}
			* ]
			==References==
⚫	]
			{{Reflist}}
		⚫	== External links ==
		⚫	*
		⚫	*
		⚫	]
	]
			]
	]
	]
	]
	]