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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

N-bromosuccinimide compound structure

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 = 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] , 7-α-hydroxysteroid dehydrogenase [Yoshimoto91] , hydrogen:menaquinone oxidoreductase [Ballantine86] , hydrogenase [Sawers86] , 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


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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