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discounted EARLY registration ends Dec 31, 2014
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MetaCyc 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): -5.1488023 Inferred by computational analysis [Latendresse13]

Enzymes activated by diethylpyrocarbonate, sorted by the type of activation, are:

Activator (Allosteric) of: malonyl-CoA:shisonin 6-O-malonyltransferase [Suzuki01b]

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

Inhibitor (Mechanism unknown) of: L-glutamine:D-fructose-6-phosphate aminotransferase [BadetDenisot92] , 3-deoxy-D-manno-octulosonate 8-phosphate synthase [Sheflyan99, Ray80a, Comment 1] , o-succinylbenzoate-CoA ligase [Bhattacharyya97, Comment 2] , sorbitol-6-phosphate dehydrogenase [Novotny84] , homoserine O-succinyltransferase [Ziegler07] , aspartate ammonia-lyase [Helmward89, Ida84] , N-acetylneuraminate lyase [Aisaka91] , N-acetyl-β-neuraminate lyase [Aisaka91] , 7-α-hydroxysteroid dehydrogenase [Yoshimoto91] , acyl-CoA thioesterase [Naggert91] , 3-hydroxybenzyl alcohol dehydrogenase [Forrester72] , 1,4-β-mannanase [Kawaguchi14] , NAD+-dependent malate dehydrogenase [Rao85] , myricetin 3-O-glucosyltransferase [Owens] , quercetin 3-O-glucosyltransferase [Owens] , kaempferol 3-O-glucosyltransferase [Owens] , (R)-mandelonitrile lyase [Wajant95] , squalene-hopene cyclase [Seckler86] , trehalase [Lee01b] , mannitol-1-phosphatase [Liberator98] , 13-hydroxylupanine O-tigloyltransferase [Okada05] , phloroglucinol reductase [Haddock89, Comment 3] , sucrose synthase [Elling95] , acetate kinase [Latimer93] , biotin sulfoxide reductase [Comment 4] , 4-coumaroyl-CoA:pelargonidin-3-O-β-D-glucoside-6''-O-acyltransferase [YonekuraSakakib00] , caffeoyl-CoA:pelargonidin-3-O-β-D-glucoside-6''-O-acyltransferase [YonekuraSakakib00] , 4-coumaroyl-CoA:cyanidin-3,5-diglucoside-6''-O-acyltransferase [YonekuraSakakib00] , 4-coumaroyl-CoA:cyanidin-3-O-β-D-glucoside-6''-O-acyltransferase [YonekuraSakakib00] , caffeoyl-CoA:pelargonidin-3,5-diglucoside-6''-O-acyltransferase [YonekuraSakakib00] , malonyl-CoA:pelargonidin-3-O-(6-caffeoyl-β-D-glucoside)-5-O-β-D-glucoside 6-O-malonyltransferase [Suzuki01b] , anthocyanin 5-O-glucoside-4'''-O-malonyltransferase [Suzuki04b] , tropinone reductase (TR-I) [Hashimoto92] , betanidin 6-O-glucosyltransferase [Vogt97]

Inhibitor (Other types) of: 3-dehydroquinate dehydratase [Chaudhuri86] , allantoate amidohydrolase [Xu95b]


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

Elling95: Elling L (1995). "Effect of metal ions on sucrose synthase from rice grains--a study on enzyme inhibition and enzyme topography." Glycobiology 1995;5(2);201-6. PMID: 7780195

Forrester72: Forrester PI, Gaucher GM (1972). "m-Hydroxybenzyl alcohol dehydrogenase from Penicillium urticae." Biochemistry 11(6);1108-14. PMID: 4335290

Haddock89: Haddock JD, Ferry JG (1989). "Purification and properties of phloroglucinol reductase from Eubacterium oxidoreducens G-41." J Biol Chem 1989;264(8);4423-7. PMID: 2925649

Hashimoto92: Hashimoto T, Nakajima K, Ongena G, Yamada Y (1992). "Two Tropinone Reductases with Distinct Stereospecificities from Cultured Roots of Hyoscyamus niger." Plant Physiol 100(2);836-845. PMID: 16653065

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

Kawaguchi14: Kawaguchi K, Senoura T, Taira T, Ito H, Wasaki J, Ito S (2014). "The mannobiose-forming exo-mannanase involved in a new mannan catabolic pathway in Bacteroides fragilis." Arch Microbiol 196(1);17-23. PMID: 24217874

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Latimer93: Latimer MT, Ferry JG (1993). "Cloning, sequence analysis, and hyperexpression of the genes encoding phosphotransacetylase and acetate kinase from Methanosarcina thermophila." J Bacteriol 1993;175(21);6822-9. PMID: 8226623

Lee01b: Lee JH, Tsuji M, Nakamura M, Nishimoto M, Okuyama M, Mori H, Kimura A, Matsui H, Chiba S (2001). "Purification and identification of the essential ionizable groups of honeybee, Apis mellifera L., trehalase." Biosci Biotechnol Biochem 65(12);2657-65. PMID: 11826961

Liberator98: Liberator P, Anderson J, Feiglin M, Sardana M, Griffin P, Schmatz D, Myers RW (1998). "Molecular cloning and functional expression of mannitol-1-phosphatase from the apicomplexan parasite Eimeria tenella." J Biol Chem 273(7);4237-44. PMID: 9461622

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

Okada05: Okada T, Hirai MY, Suzuki H, Yamazaki M, Saito K (2005). "Molecular characterization of a novel quinolizidine alkaloid O-tigloyltransferase: cDNA cloning, catalytic activity of recombinant protein and expression analysis in Lupinus plants." Plant Cell Physiol 46(1);233-44. PMID: 15659437

Owens: Owens DK, McIntosh CA "Identification, recombinant expression, and biochemical characterization of a flavonol 3-O-glucosyltransferase clone from Citrus paradisi." Phytochemistry 70(11-12);1382-91. PMID: 19733370

Pollock01: Pollock, VV, Barber, MJ "Kinetic and mechanistic properties of biotin sulfoxide reductase." Biochemistry 40:1430-1440 (2001).

Rao85: Rao JG, Harris BG, Cook PF (1985). "Diethylpyrocarbonate inactivation of NAD-malic enzyme from Ascaris suum." Arch Biochem Biophys 241(1);67-74. PMID: 4026323

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

Seckler86: Seckler B, Poralla K (1986). "Characterization and partial purification of squalene-hopene cyclase from Bacillus acidocaldarius." Biochimica et Biophysica Acta (BBA) - General Subjects 881(3);356-363.

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

Suzuki01b: Suzuki H, Nakayama T, Yonekura-Sakakibara K, Fukui Y, Nakamura N, Nakao M, Tanaka Y, Yamaguchi MA, Kusumi T, Nishino T (2001). "Malonyl-CoA:anthocyanin 5-O-glucoside-6"'-O-malonyltransferase from scarlet sage (Salvia splendens) flowers. Enzyme purification, gene cloning, expression, and characterization." J Biol Chem 276(52);49013-9. PMID: 11598135

Suzuki04b: Suzuki H, Sawada S, Watanabe K, Nagae S, Yamaguchi MA, Nakayama T, Nishino T (2004). "Identification and characterization of a novel anthocyanin malonyltransferase from scarlet sage (Salvia splendens) flowers: an enzyme that is phylogenetically separated from other anthocyanin acyltransferases." Plant J 38(6);994-1003. PMID: 15165190

Vogt97: Vogt T, Zimmermann E, Grimm R, Meyer M, Strack D (1997). "Are the characteristics of betanidin glucosyltransferases from cell-suspension cultures of Dorotheanthus bellidiformis indicative of their phylogenetic relationship with flavonoid glucosyltransferases?." Planta 203(3);349-61. PMID: 9431682

Wajant95: Wajant H, Forster S, Selmar D, Effenberger F, Pfizenmaier K (1995). "Purification and Characterization of a Novel (R)-Mandelonitrile Lyase from the Fern Phlebodium aureum." Plant Physiol 109(4);1231-1238. PMID: 12228664

Xu95b: Xu Z, de Windt FE, van der Drift C (1995). "Purification and characterization of allantoate amidohydrolase from Bacillus fastidiosus." Arch Biochem Biophys 324(1);99-104. PMID: 7503567

YonekuraSakakib00: Yonekura-Sakakibara K, Tanaka Y, Fukuchi-Mizutani M, Fujiwara H, Fukui Y, Ashikari T, Murakami Y, Yamaguchi M, Kusumi T (2000). "Molecular and biochemical characterization of a novel hydroxycinnamoyl-CoA: anthocyanin 3-O-glucoside-6"-O-acyltransferase from Perilla frutescens." Plant Cell Physiol 41(4);495-502. PMID: 10845463

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 MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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