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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
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MetaCyc Compound: N-bromosuccinimide

Superclasses: an organohalogen compound an organobromine compound

Chemical Formula: C4H4NO2Br

Molecular Weight: 177.98 Daltons

Monoisotopic Molecular Weight: 176.94254097779998 Daltons

SMILES: C1(C(N(C(C1)=O)Br)=O)

InChI: InChI=1S/C4H4BrNO2/c5-6-3(7)1-2-4(6)8/h1-2H2

InChIKey: InChIKey=PCLIMKBDDGJMGD-UHFFFAOYSA-N

Unification Links: ChEBI:53174 , ChemSpider:60528 , PubChem:67184

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -6.9055176 Inferred by computational analysis [Latendresse13]

In Reactions of unknown directionality:

Not in pathways:
an organic molecule + hydrogen bromide + hydrogen peroxide + H+ = an organobromine compound + 2 H2O

Enzymes inhibited by N-bromosuccinimide, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: N-acetylneuraminate lyase [Aisaka91, Uchida84] , N-acetyl-β-neuraminate lyase [Aisaka91, Uchida84] , hydrogenase [Ballantine86] , hydrogenase [Sawers86] , 7-α-hydroxysteroid dehydrogenase [Yoshimoto91] , cellobiose 2-epimerase [Taguchi08] , 1,4-β-mannanase [Kawaguchi14] , quercetin 3-O-glucosyltransferase [Owens] , kaempferol 3-O-glucosyltransferase [Owens] , myricetin 3-O-glucosyltransferase [Owens] , N-acetylneuraminate synthase [Komaki97]

Inhibitor (Other types) of: endo-1,3-β-xylanase , nucleoside oxidase [Isono89]


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

Ballantine86: Ballantine SP, Boxer DH (1986). "Isolation and characterisation of a soluble active fragment of hydrogenase isoenzyme 2 from the membranes of anaerobically grown Escherichia coli." Eur J Biochem 1986;156(2);277-84. PMID: 3516690

Isono89: Isono, Y., Sudo, T., Hoshino, M. (1989). "Properties of a new enzyme, nucleoside oxidase, from Pseudomonas maltophilia LB-86." Agric. Biol. Chem. 53:1671-1677.

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

Komaki97: Komaki E, Ohta Y, Tsukada Y (1997). "Purification and characterization of N-acetylneuraminate synthase from Escherichia coli K1-M12." Biosci Biotechnol Biochem 61(12);2046-50. PMID: 9438985

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

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

Sawers86: Sawers RG, Boxer DH (1986). "Purification and properties of membrane-bound hydrogenase isoenzyme 1 from anaerobically grown Escherichia coli K12." Eur J Biochem 1986;156(2);265-75. PMID: 3516689

Taguchi08: Taguchi H, Hamada S, Kawauchi S, Ito H, Senoura T, Watanabe J, Nishimukai M, Ito S, Matsui H (2008). "Enzymatic properties of cellobiose 2-epimerase from Ruminococcus albus and the synthesis of rare oligosaccharides by the enzyme." Appl Microbiol Biotechnol 79(3);433-41. PMID: 18392616

Uchida84: Uchida Y, Tsukada Y, Sugimori T (1984). "Purification and properties of N-acetylneuraminate lyase from Escherichia coli." J Biochem 96(2);507-22. PMID: 6389524

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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Sat Nov 22, 2014, BIOCYC14A.