Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

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, Suzuki73] , 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

Suzuki73: 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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 18.5 on Wed Nov 26, 2014, biocyc13.