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Escherichia coli K-12 substr. MG1655 Compound: iodoacetamide

Synonyms: iodoacetoamide, 2-iodoacetamide, acetamide, 2-iodo-, monoiodoacetamide, surauto, N-(3-methoxy-4-butoxybenzyl)thiobarbituric acid

Superclasses: an organohalogen compound an organoiodine compound

Chemical Formula: C2H4NOI

Molecular Weight: 184.96 Daltons

Monoisotopic Molecular Weight: 184.9337567557 Daltons

SMILES: C(I)C(N)=O

InChI: InChI=1S/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5)

InChIKey: InChIKey=PGLTVOMIXTUURA-UHFFFAOYSA-N

Unification Links: ChEBI:103838 , ChemSpider:3596 , PubChem:3727

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -39.04

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

Inhibitor (Irreversible) of: L-glutamine:D-fructose-6-phosphate aminotransferase [Badet87]

Inhibitor (Mechanism unknown) of: amidophosphoribosyl transferase [Messenger79] , farnesyl diphosphate synthase [Fujisaki86] , geranyl diphosphate synthase [Fujisaki86] , β-ketoacyl-ACP synthase [Greenspan69, Comment 1] , acetyl-CoA:ACP transacylase [Lowe88] , glutathionylspermidine amidase [Lin97] , acetoacetyl-[acp] synthase [Greenspan69, Comment 1] , acyl-CoA thioesterase [Naggert91] , homoserine O-succinyltransferase [Born99, Comment 2] , malonyl-CoA-ACP transacylase [Ruch73] , 3-ketoacyl-CoA thiolase [Yang83] , isopentenyl diphosphate isomerase [Fujisaki86, Comment 3] , glucosamine-1-phosphate acetyltransferase [Pompeo98] , formate dehydrogenase-N


References

Badet87: Badet B, Vermoote P, Haumont PY, Lederer F, LeGoffic F (1987). "Glucosamine synthetase from Escherichia coli: purification, properties, and glutamine-utilizing site location." Biochemistry 1987;26(7);1940-8. PMID: 3297136

Born99: Born TL, Blanchard JS (1999). "Enzyme-catalyzed acylation of homoserine: mechanistic characterization of the Escherichia coli metA-encoded homoserine transsuccinylase." Biochemistry 1999;38(43);14416-23. PMID: 10572016

Fujisaki86: Fujisaki S, Nishino T, Katsuki H (1986). "Isoprenoid synthesis in Escherichia coli. Separation and partial purification of four enzymes involved in the synthesis." J Biochem (Tokyo) 1986;99(5);1327-37. PMID: 3519603

Greenspan69: Greenspan MD, Alberts AW, Vagelos PR (1969). "Acyl carrier protein. 13. Beta-ketoacyl acyl carrier protein synthetase from Escherichia coli." J Biol Chem 1969;244(23);6477-85. PMID: 4901371

Lin97: Lin CH, Kwon DS, Bollinger JM, Walsh CT (1997). "Evidence for a glutathionyl-enzyme intermediate in the amidase activity of the bifunctional glutathionylspermidine synthetase/amidase from Escherichia coli." Biochemistry 36(48);14930-8. PMID: 9398217

Lowe88: Lowe PN, Rhodes S (1988). "Purification and characterization of [acyl-carrier-protein] acetyltransferase from Escherichia coli." Biochem J 1988;250(3);789-96. PMID: 3291856

Messenger79: Messenger LJ, Zalkin H (1979). "Glutamine phosphoribosylpyrophosphate amidotransferase from Escherichia coli. Purification and properties." J Biol Chem 1979;254(9);3382-92. PMID: 372191

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

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

Ruch73: Ruch FE, Vagelos PR (1973). "The isolation and general properties of Escherichia coli malonyl coenzyme A-acyl carrier protein transacylase." J Biol Chem 1973;248(23);8086-94. PMID: 4584822

Yang83: Yang SY, Schulz H (1983). "The large subunit of the fatty acid oxidation complex from Escherichia coli is a multifunctional polypeptide. Evidence for the existence of a fatty acid oxidation operon (fad AB) in Escherichia coli." J Biol Chem 1983;258(16);9780-5. PMID: 6350283


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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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