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Escherichia coli K-12 substr. MG1655 Compound: iodoacetate

Synonyms: 2-iodoacetate, monoiodoacetate

Superclasses: an organohalogen compound an organoiodine compound

Chemical Formula: C2H2O2I

Molecular Weight: 184.94 Daltons

Monoisotopic Molecular Weight: 185.9177723405 Daltons

iodoacetate compound structure

SMILES: C(I)C(=O)[O-]

InChI: InChI=1S/C2H3IO2/c3-1-2(4)5/h1H2,(H,4,5)/p-1

InChIKey: InChIKey=JDNTWHVOXJZDSN-UHFFFAOYSA-M

Unification Links: ChemSpider:452795 , PubChem:519093

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -81.48

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

Inhibitor (Noncompetitive) of: aspartate semialdehyde dehydrogenase [Hegeman70, Helmward89]

Inhibitor (Mechanism unknown) of: riboflavin reductase [Fontecave87] , glyceraldehyde 3-phosphate dehydrogenase [DAlessio71a] , NADPH-dependent curcumin reductase [Hassaninasab11] , biotin sulfoxide reductase [Del79] , 2-keto-4-hydroxyglutarate aldolase , glycogen phosphorylase-limit dextrin α-1,6-glucohydrolase [Jeanningros76] , 2,3,4-saturated fatty acyl-[acp]:NAD+ oxidoreductase [Weeks68] , ribose-5-phosphate isomerase [Essenberg75] , glycerate kinase [Doughty66] , lactaldehyde dehydrogenase [Sridhara69] , S-formylglutathione hydrolase [Gonzalez06] , S-formylglutathione hydrolase [Gonzalez06]

Inhibitor (Other types) of: biotin transporter [Prakash74]

This compound has been characterized as an alternative substrate of the following enzymes: bromoacetate dehalogenase


References

DAlessio71a: D'Alessio G, Josse J (1971). "Glyceraldehyde phosphate dehydrogenase of Escherichia coli. Structural and catalytic properties." J Biol Chem 246(13);4326-33. PMID: 4326214

Del79: Del Campillo-Campbell, A, Dykhuizen, D, Cleary, PP "Enzymatic reduction of d-biotin d-sulfoxide to d-biotin." Methods in Enzymology 62:379-385 (1979).

Doughty66: Doughty CC, Hayashi JA, Guenther HL (1966). "Purification and properties of D-glycerate 3-kinase from Escherichia coli." J Biol Chem 1966;241(3);568-72. PMID: 5325263

Essenberg75: Essenberg MK, Cooper RA (1975). "Two ribose-5-phosphate isomerases from Escherichia coli K-12: partial chacterisation of the enzymes and consideration of their possible physiological roles." Eur J Biochem 1975;55:323-332. PMID: 1104357

Fontecave87: Fontecave M, Eliasson R, Reichard P (1987). "NAD(P)H:flavin oxidoreductase of Escherichia coli. A ferric iron reductase participating in the generation of the free radical of ribonucleotide reductase." J Biol Chem 1987;262(25);12325-31. PMID: 3305505

Gonzalez06: Gonzalez CF, Proudfoot M, Brown G, Korniyenko Y, Mori H, Savchenko AV, Yakunin AF (2006). "Molecular basis of formaldehyde detoxification: Characterization of two s-formylglutathione hydrolases from Escherichia coli, FrmB and YeiG." J Biol Chem 281:14514-14522. PMID: 16567800

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

Hegeman70: Hegeman G, Cohen G, Morgan R "Aspartic semialdehyde dehydrogenase (Escherichia coli K12)." Methods in Enzymology 1970; 17A:708-713.

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

Jeanningros76: Jeanningros R, Creuzet-Sigal N, Frixon C, Cattaneo J (1976). "Purification and properties of a debranching enzyme from Escherichia coli." Biochim Biophys Acta 1976;438(1);186-99. PMID: 779849

Prakash74: Prakash O, Eisenberg MA (1974). "Active transport of biotin in Escherichia coli K-12." J Bacteriol 120(2);785-91. PMID: 4616949

Sridhara69: Sridhara S, Wu TT (1969). "Purification and properties of lactaldehyde dehydrogenase from Escherichia coli." J Biol Chem 1969;244(19);5233-8. PMID: 4310089

Weeks68: Weeks G, Wakil SJ (1968). "Studies on the mechanism of fatty acid synthesis. 18. Preparation and general properties of the enoyl acyl carrier protein reductases from Escherichia coli." J Biol Chem 1968;243(6);1180-9. PMID: 4384650


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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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