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Escherichia coli K-12 substr. MG1655 Compound: 5,5'-dithio-bis-2-nitrobenzoate

Synonyms: dithionitrobenzoic acid, dithionitrobenzoate, DTNB, 5-(3-carboxy-4-nitro-phenyl)disulfanyl-2-nitro-benzoic acid, 5'-dithio-bis(2-nitrobenzoic acid), 5,5'-dithio-bis(2-nitrobenzoic acid)

Superclasses: a nitrohydrocarbon a C-nitro compound

Chemical Formula: C14H6N2O8S2

Molecular Weight: 394.33 Daltons

Monoisotopic Molecular Weight: 397.9878566882 Daltons

SMILES: C1(C=C(C(=CC=1SSC2(=CC=C(C(=C2)C(=O)[O-])[N+]([O-])=O))C(=O)[O-])[N+]([O-])=O)

InChI: InChI=1S/C14H8N2O8S2/c17-13(18)9-5-7(1-3-11(9)15(21)22)25-26-8-2-4-12(16(23)24)10(6-8)14(19)20/h1-6H,(H,17,18)(H,19,20)/p-2

InChIKey: InChIKey=KIUMMUBSPKGMOY-UHFFFAOYSA-L

Unification Links: ChemSpider:5367523 , PubChem:7000011

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -223.53

Enzymes inhibited by 5,5'-dithio-bis-2-nitrobenzoate, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: glycerol-3-phosphate dehydrogenase, anaerobic [Schryvers81] , 3-(2,3-dihydroxyphenyl)propionate 1,2-dioxygenase [Spence96] , 5,10-methylenetetrahydrofolate:glycine hydroxymethyltransferase [JoshiTope90, Schirch85] , NADPH-dependent curcumin reductase [Hassaninasab11] , tRNA-guanine transglycosylase [Garcia97] , prephenate dehydratase [Gething77] , glucosamine-1-phosphate acetyltransferase [Pompeo98, Comment 1] , aspartate ammonia-lyase [Helmward89, Suzuki73a] , 6-phosphogluconate dehydrogenase , threonine dehydrogenase [Boylan81] , 4-aminobutyrate transaminase [Schulz90] , xanthosine-5'-phosphate:L-glutamine amido-ligase (AMP-forming) [Patel77] , trans-2-enoyl-CoA reductase [Nishimaki84] , aspartate semialdehyde dehydrogenase [Alvarez04] , isocitrate lyase , glutathione synthetase [Kato88] , cyclopropane fatty acyl phospholipid synthase [Taylor79, Grogan97] , glyoxalase [Misra95, Comment 2]


References

Alvarez04: Alvarez E, Ramon F, Magan C, Diez E (2004). "L-cystine inhibits aspartate-beta-semialdehyde dehydrogenase by covalently binding to the essential 135Cys of the enzyme." Biochim Biophys Acta 1696(1);23-9. PMID: 14726201

Boylan81: Boylan SA, Dekker EE (1981). "L-threonine dehydrogenase. Purification and properties of the homogeneous enzyme from Escherichia coli K-12." J Biol Chem 1981;256(4);1809-15. PMID: 6780553

Garcia97: Garcia GA, Chong S (1997). "Cysteine 265 is in the active site of, but is not essential for catalysis by tRNA-guanine transglycosylase (TGT) from Escherichia coli." J Protein Chem 16(1);11-7. PMID: 9055203

Gething77: Gething MJ, Davidson BE (1977). "Chorismate mutase/prephenate dehydratase from Escherichia coli K12. Modification with 5,5'-dithio-bis(2-nitrobenzoic acid)." Eur J Biochem 1977;78(1);103-10. PMID: 334529

Grogan97: Grogan DW, Cronan JE (1997). "Cyclopropane ring formation in membrane lipids of bacteria." Microbiol Mol Biol Rev 1997;61(4);429-41. PMID: 9409147

Hassaninasab11: Hassaninasab A, Hashimoto Y, Tomita-Yokotani K, Kobayashi M (2011). "Discovery of the curcumin metabolic pathway involving a unique enzyme in an intestinal microorganism." Proc Natl Acad Sci U S A 108(16):6615-20. PMID: 21467222

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

JoshiTope90: Joshi-Tope G, Schirch V (1990). "The role of a critical sulfhydryl group in the mechanism of serine hydroxymethyltransferase." Ann N Y Acad Sci 585;339-45. PMID: 2113366

Kato88: Kato H, Tanaka T, Nishioka T, Kimura A, Oda J (1988). "Role of cysteine residues in glutathione synthetase from Escherichia coli B. Chemical modification and oligonucleotide site-directed mutagenesis." J Biol Chem 1988;263(24);11646-51. PMID: 3042775

Misra95: Misra K, Banerjee AB, Ray S, Ray M (1995). "Glyoxalase III from Escherichia coli: a single novel enzyme for the conversion of methylglyoxal into D-lactate without reduced glutathione." Biochem J 1995;305 ( Pt 3);999-1003. PMID: 7848303

Nishimaki84: Nishimaki T, Yamanaka H, Mizugaki M (1984). "Studies on the metabolism of unsaturated fatty acids. XIV. Purification and properties of NADPH-dependent trans-2-enoyl-CoA reductase of Escherichia coli K-12." J Biochem (Tokyo) 1984;95(5);1315-21. PMID: 6378898

Patel77: Patel N, Moyed HS, Kane JF (1977). "Properties of xanthosine 5'-monophosphate-amidotransferase from Escherichia coli." Arch Biochem Biophys 1977;178(2);652-61. PMID: 189701

Pompeo98: Pompeo F, van Heijenoort J, Mengin-Lecreulx D (1998). "Probing the role of cysteine residues in glucosamine-1-phosphate acetyltransferase activity of the bifunctional GlmU protein from Escherichia coli: site-directed mutagenesis and characterization of the mutant enzymes." J Bacteriol 1998;180(18);4799-803. PMID: 9733680

Schirch85: Schirch V, Hopkins S, Villar E, Angelaccio S (1985). "Serine hydroxymethyltransferase from Escherichia coli: purification and properties." J Bacteriol 1985;163(1);1-7. PMID: 3891721

Schryvers81: Schryvers A, Weiner JH (1981). "The anaerobic sn-glycerol-3-phosphate dehydrogenase of Escherichia coli. Purification and characterization." J Biol Chem 1981;256(19);9959-65. PMID: 6792201

Schulz90: Schulz A, Taggeselle P, Tripier D, Bartsch K (1990). "Stereospecific production of the herbicide phosphinothricin (glufosinate) by transamination: isolation and characterization of a phosphinothricin-specific transaminase from Escherichia coli." Appl Environ Microbiol 1990;56(1);1-6. PMID: 2178550

Spence96: Spence EL, Kawamukai M, Sanvoisin J, Braven H, Bugg TD (1996). "Catechol dioxygenases from Escherichia coli (MhpB) and Alcaligenes eutrophus (MpcI): sequence analysis and biochemical properties of a third family of extradiol dioxygenases." J Bacteriol 1996;178(17);5249-56. PMID: 8752345

Suzuki73a: Suzuki S, Yamaguchi J, Tokushige M (1973). "Studies on aspartase. I. Purification and molecular properties of aspartase from Escherichia coli." Biochim Biophys Acta 1973;321(1);369-81. PMID: 4584395

Taylor79: Taylor FR, Cronan JE (1979). "Cyclopropane fatty acid synthase of Escherichia coli. Stabilization, purification, and interaction with phospholipid vesicles." Biochemistry 1979;18(15);3292-300. PMID: 380648


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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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