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Escherichia coli K-12 substr. MG1655 Compound: diethylpyrocarbonate

Synonyms: DEPC

Chemical Formula: C6H10O5

Molecular Weight: 162.14 Daltons

Monoisotopic Molecular Weight: 162.0528234315 Daltons

SMILES: CCOC(OC(OCC)=O)=O

InChI: InChI=1S/C6H10O5/c1-3-9-5(7)11-6(8)10-4-2/h3-4H2,1-2H3

InChIKey: InChIKey=FFYPMLJYZAEMQB-UHFFFAOYSA-N

Unification Links: ChEBI:59051 , ChemSpider:2943 , HMDB:HMDB32873 , KEGG:C11592 , PubChem:3051

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -107.86

Enzymes inhibited by diethylpyrocarbonate, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: N-acetyl-β-neuraminate lyase [Aisaka91] , homoserine O-succinyltransferase [Ziegler07] , acyl-CoA thioesterase [Naggert91] , 3-deoxy-D-manno-octulosonate 8-phosphate synthase [Sheflyan99, Ray80a, Comment 1] , L-glutamine:D-fructose-6-phosphate aminotransferase [BadetDenisot92] , sorbitol-6-phosphate dehydrogenase [Novotny84] , N-acetylneuraminate lyase [Aisaka91] , aspartate ammonia-lyase [Helmward89, Ida84] , o-succinylbenzoate-CoA ligase [Bhattacharyya97, Comment 2] , 7-α-hydroxysteroid dehydrogenase [Yoshimoto91]

Inhibitor (Other types) of: 3-dehydroquinate dehydratase [Chaudhuri86]


References

Aisaka91: Aisaka K, Igarashi A, Yamaguchi K, Uwajima T (1991). "Purification, crystallization and characterization of N-acetylneuraminate lyase from Escherichia coli." Biochem J 1991;276 ( Pt 2);541-6. PMID: 1646603

BadetDenisot92: Badet-Denisot MA, Badet B (1992). "Chemical modification of glucosamine-6-phosphate synthase by diethyl pyrocarbonate: evidence of histidine requirement for enzymatic activity." Arch Biochem Biophys 1992;292(2);475-8. PMID: 1731613

Bhattacharyya97: Bhattacharyya DK, Kwon O, Meganathan R (1997). "Vitamin K2 (menaquinone) biosynthesis in Escherichia coli: evidence for the presence of an essential histidine residue in o-succinylbenzoyl coenzyme A synthetase." J Bacteriol 1997;179(19);6061-5. PMID: 9324253

Chaudhuri86: Chaudhuri S, Lambert JM, McColl LA, Coggins JR (1986). "Purification and characterization of 3-dehydroquinase from Escherichia coli." Biochem J 1986;239(3);699-704. PMID: 2950851

Helmward89: Helmward Z "Handbook of Enzyme Inhibitors. 2nd, revised and enlarged edition." Weinheim, Federal Republic of Germany ; New York, NY, USA , 1989.

Ida84: Ida N, Tokushige M (1984). "Chemical modification of essential histidine residues in aspartase with diethylpyrocarbonate." J Biochem (Tokyo) 1984;96(5);1315-21. PMID: 6396297

Naggert91: Naggert J, Narasimhan ML, DeVeaux L, Cho H, Randhawa ZI, Cronan JE, Green BN, Smith S (1991). "Cloning, sequencing, and characterization of Escherichia coli thioesterase II." J Biol Chem 1991;266(17);11044-50. PMID: 1645722

Novotny84: Novotny MJ, Reizer J, Esch F, Saier MH (1984). "Purification and properties of D-mannitol-1-phosphate dehydrogenase and D-glucitol-6-phosphate dehydrogenase from Escherichia coli." J Bacteriol 1984;159(3);986-90. PMID: 6384188

Ray80a: Ray PH (1980). "Purification and characterization of 3-deoxy-D-manno-octulosonate 8-phosphate synthetase from Escherichia coli." J Bacteriol 1980;141(2);635-44. PMID: 6988389

Sheflyan99: Sheflyan GY, Duewel HS, Chen G, Woodard RW (1999). "Identification of essential histidine residues in 3-deoxy-D-manno-octulosonic acid 8-phosphate synthase: analysis by chemical modification with diethyl pyrocarbonate and site-directed mutagenesis." Biochemistry 1999;38(43);14320-9. PMID: 10572007

Yoshimoto91: Yoshimoto T, Higashi H, Kanatani A, Lin XS, Nagai H, Oyama H, Kurazono K, Tsuru D (1991). "Cloning and sequencing of the 7 alpha-hydroxysteroid dehydrogenase gene from Escherichia coli HB101 and characterization of the expressed enzyme." J Bacteriol 1991;173(7);2173-9. PMID: 2007545

Ziegler07: Ziegler K, Noble SM, Mutumanje E, Bishop B, Huddler DP, Born TL (2007). "Identification of catalytic cysteine, histidine, and lysine residues in Escherichia coli homoserine transsuccinylase." Biochemistry 46(10);2674-83. PMID: 17302437


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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