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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: 2-mercaptoethanol

Synonyms: hydroxyethyl sulfide, β-mercaptoethanol

Chemical Formula: C2H6OS

Molecular Weight: 78.129 Daltons

Monoisotopic Molecular Weight: 78.0139355047 Daltons

SMILES: C(O)CS

InChI: InChI=1S/C2H6OS/c3-1-2-4/h3-4H,1-2H2

InChIKey: InChIKey=DGVVWUTYPXICAM-UHFFFAOYSA-N

Unification Links: ChEBI:41218 , ChemSpider:1512 , DrugBank:DB03345 , KEGG:C00928 , PubChem:1567

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 22.626724 Inferred by computational analysis [Latendresse13]

In Reactions of unknown directionality:

Not in pathways:
2-hydroxyethyldisulfide + 2 glutathione = 2 2-mercaptoethanol + glutathione disulfide

Enzymes activated by 2-mercaptoethanol, sorted by the type of activation, are:

Activator (Mechanism unknown) of: α-galactosidase [Burstein71] , thymidylate synthase [Haertle79] , galactarate dehydratase [Hubbard98] , galactokinase [Sherman63] , methylglyoxal reductase (NADPH-dependent) [Saikusa87] , dihydropterin oxidase [Unnasch82] , glycerophosphocholine cholinephosphodiesterase [Sugimori13] , o-dihydric phenol O-methyltransferase (para-methylation) [Tsang79] , esculetin 6-O-methyltransferase (meta-methylation) [Tsang79] , esculetin 7-O-glucosyltransferase [Taguchi00] , agmatine coumaroyltransferase [Burhenne03] , cytidine 5'-monophosphate N-acetylneuraminate synthetase [RodriguezAparic92] , oleanolate UDP-glucuronosyltransferase [Wojciechowski75] , isopenicillin N epimerase [Usui89] , L-gulono-γ-lactone oxidase [Nishikimi79] , imidazoleglycerolphosphate dehydratase [Tada95] , ornithine carbamoyltransferase [Morizono97] , alkenyl thiohydroximate-O-sulfate sulfohydrolase (epithionitrile-forming) [Burow06] , thiohydroximate-O-sulfate sulfohydrolase (nitrile-forming) [Burow06] , benzalacetone synthase [BorejszaWysocki96]

Enzymes inhibited by 2-mercaptoethanol, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: peroxygenase [Hanano06] , ribitol dehydrogenase [Taylor74]

Inhibitor (Mechanism unknown) of: D-galacturonate isomerase [Ashwell60] , D-glucuronate isomerase [Ashwell60] , threonine dehydrogenase [Comment 1] , methylenetetrahydrofolate dehydrogenase [DAri91] , lactose galactohydrolase [Wallenfels72] , dihydrobenzophenanthridine oxidase [Arakawa92] , dihydrobenzophenanthridine oxidase [Arakawa92a] , dihydrogeodin oxidase [Fujii87] , ethylnitronate monooxygenase [Gorlatova98] , sinapoylglucose:sinapoylglucose O-sinapoyltransferase [Dahlbender86] , glycerol dehydrogenase [McGregor74] , UDP-D-xylose synthase [Baron72] , UDP-D-apiose synthase [Baron72] , thiosulfite-cleaving enzyme [Fukumori89] , tellimagrandin II: O2 oxidoreductase [Niemetz03a] , β-glucogallin O-galloyltransferase [Schmidt87] , pentagalloylglucose: O2 oxidoreductase [Niemetz03b]

Inhibitor (Other types) of: indole-3-acetaldoxime dehydratase [Shukla68]


References

Arakawa92: Arakawa H, Clark WG, Psenak M, Coscia CJ (1992). "Purification and characterization of dihydrobenzophenanthridine oxidase from elicited Sanguinaria canadensis cell cultures." Arch Biochem Biophys 299(1);1-7. PMID: 1444440

Arakawa92a: Arakawa, Hirohumi, Clark, Gregg, Psenak, Mikulas, Coscia, Carmine (1992). "Purification and characterization of dihydrobenzophenanthridine oxidase from elicited Sanguinaria canadensis cell cultures." Archives of Biochemistry and Biophysics, 299(1):1-7.

Ashwell60: Ashwell G, Wahba AJ, Hickman J (1960). "Uronic acid metabolism in bacteria. I. Purification and properties of uronic acid isomerase in Escherichia coli." J Biol Chem. 235:1559-1565. PMID: 13794771

Baron72: Baron D, Wellmann E, Grisebach H (1972). "Purification and properties of an enzyme from cell suspension cultures of parsley catalyzing the synthesis of UDP-apiose and UDP-D-xylose from UDP-D-glucuronic acid." Biochim Biophys Acta 258(1);310-8. PMID: 4333589

BorejszaWysocki96: Borejsza-Wysocki W, Hrazdina G (1996). "Aromatic Polyketide Synthases (Purification, Characterization, and Antibody Development to Benzalacetone Synthase from Raspberry Fruits)." Plant Physiol 110(3);791-799. PMID: 12226219

Burhenne03: Burhenne K, Kristensen BK, Rasmussen SK (2003). "A new class of N-hydroxycinnamoyltransferases. Purification, cloning, and expression of a barley agmatine coumaroyltransferase (EC 2.3.1.64)." J Biol Chem 278(16);13919-27. PMID: 12582168

Burow06: Burow M, Markert J, Gershenzon J, Wittstock U (2006). "Comparative biochemical characterization of nitrile-forming proteins from plants and insects that alter myrosinase-catalysed hydrolysis of glucosinolates." FEBS J 273(11);2432-46. PMID: 16704417

Burstein71: Burstein C, Kepes A (1971). "The alpha-galactosidase from Escherichia coli K12." Biochim Biophys Acta 1971;230(1);52-63. PMID: 5543331

Craig88: Craig PA, Dekker EE (1988). "Cd2+ activation of L-threonine dehydrogenase from Escherichia coli K-12." Biochim Biophys Acta 1988;957(2);222-9. PMID: 3056527

Dahlbender86: Dahlbender, B. and Strack, D. (1986). "Purification and properties of 1-(hydroxycinnamoyl)-glucose:1-(hydroxycinnamoyl)-glucose hydroxycinnamoyltransferase from radish seedlings." Phytochemistry 25:1043-1046 doi:10.1016/S0031-9422(00)81550-2.

DAri91: D'Ari L, Rabinowitz JC (1991). "Purification, characterization, cloning, and amino acid sequence of the bifunctional enzyme 5,10-methylenetetrahydrofolate dehydrogenase/5,10-methenyltetrahydrofolate cyclohydrolase from Escherichia coli." J Biol Chem 1991;266(35);23953-8. PMID: 1748668

Fujii87: Fujii I, Iijima H, Tsukita S, Ebizuka Y, Sankawa U (1987). "Purification and properties of dihydrogeodin oxidase from Aspergillus terreus." J Biochem 101(1);11-8. PMID: 3032923

Fukumori89: Fukumori Y, Hoshiko K, Yamanaka T (1989). "Purification and some properties of thiosulphate-cleaving enzyme from Thiobacillus novellus." FEMS Microbiol Lett 65:159-164. PMID: 2612884

Gorlatova98: Gorlatova N, Tchorzewski M, Kurihara T, Soda K, Esaki N (1998). "Purification, characterization, and mechanism of a flavin mononucleotide-dependent 2-nitropropane dioxygenase from Neurospora crassa." Appl Environ Microbiol 1998;64(3);1029-33. PMID: 9501443

Haertle79: Haertle T, Wohlrab F, Guschlbauer W (1979). "Thymidylate synthetase from Escherichia coli K12. Purification, and dependence of kinetic properties on sugar conformation and size of the 2' substituent." Eur J Biochem 1979;102(1);223-30. PMID: 42538

Hanano06: Hanano A, Burcklen M, Flenet M, Ivancich A, Louwagie M, Garin J, Blee E (2006). "Plant seed peroxygenase is an original heme-oxygenase with an EF-hand calcium binding motif." J Biol Chem 281(44);33140-51. PMID: 16956885

Hubbard98: Hubbard BK, Koch M, Palmer DR, Babbitt PC, Gerlt JA (1998). "Evolution of enzymatic activities in the enolase superfamily: characterization of the (D)-glucarate/galactarate catabolic pathway in Escherichia coli." Biochemistry 1998;37(41);14369-75. PMID: 9772162

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

McGregor74: McGregor WG, Phillips J, Suelter CH (1974). "Purification and kinetic characterization of a monovalent cation-activated glycerol dehydrogenase from Aerobacter aerogenes." J Biol Chem 249(10);3132-9. PMID: 4364415

Morizono97: Morizono H, Tuchman M, Rajagopal BS, McCann MT, Listrom CD, Yuan X, Venugopal D, Barany G, Allewell NM (1997). "Expression, purification and kinetic characterization of wild-type human ornithine transcarbamylase and a recurrent mutant that produces 'late onset' hyperammonaemia." Biochem J 322 ( Pt 2);625-31. PMID: 9065786

Niemetz03a: Niemetz R, Gross GG (2003). "Ellagitannin biosynthesis: laccase-catalyzed dimerization of tellimagrandin II to cornusiin E in Tellima grandiflora." Phytochemistry 64(7);1197-201. PMID: 14599517

Niemetz03b: Niemetz R, Gross GG (2003). "Oxidation of pentagalloylglucose to the ellagitannin, tellimagrandin II, by a phenol oxidase from Tellima grandiflora leaves." Phytochemistry 62(3);301-6. PMID: 12620341

Nishikimi79: Nishikimi M (1979). "L-Gulono-gamma-lactone oxidase (rat and goat liver)." Methods Enzymol 62;24-30. PMID: 440104

RodriguezAparic92: Rodriguez-Aparicio LB, Luengo JM, Gonzalez-Clemente C, Reglero A (1992). "Purification and characterization of the nuclear cytidine 5'-monophosphate N-acetylneuraminic acid synthetase from rat liver." J Biol Chem 267(13);9257-63. PMID: 1577759

Saikusa87: Saikusa T, Rhee H, Watanabe K, Murata K, Kimura A (1987). "Metabolism of 2-oxoaldehydes in bacteria: purification and characterization of methylglyoxal reductase from E. coli." Agricultural and Biological Chemistry 51(7): 1893-1899.

Schmidt87: Schmidt SW, Denzel K, Schilling G, Gross GG (1987). "Enzymatic synthesis of 1,6-digalloylglucose from β-glucogallin by β-glucogallin: β-glucogallin 6-O-galloyltransferase from Oak leaves." Z. Naturforsch., 42c, 87-92.

Sherman63: Sherman JR, Adler J "Galactokinase from Escherichia coli." J Biol Chem 1963;238(3);873-878. PMID: 13977183

Shukla68: Shukla PS, Mahadevan S (1968). "Indoleacetaldoxime hydro-lyase. II. Purification and properties." Arch Biochem Biophys 125(3);873-83. PMID: 5671050

Sugimori13: Sugimori D, Ogasawara J, Okuda K, Murayama K (2013). "Purification, characterization, molecular cloning, and extracellular production of a novel bacterial glycerophosphocholine cholinephosphodiesterase from Streptomyces sanglieri." J Biosci Bioeng. PMID: 24211038

Tada95: Tada S, Hatano M, Nakayama Y, Volrath S, Guyer D, Ward E, Ohta D (1995). "Insect cell expression of recombinant imidazoleglycerolphosphate dehydratase of Arabidopsis and wheat and inhibition by triazole herbicides." Plant Physiol 109(1);153-9. PMID: 7480319

Taguchi00: Taguchi G, Imura H, Maeda Y, Kodaira R, Hayashida N, Shimosaka M, Okazaki M (2000). "Purification and characterization of UDP-glucose: hydroxycoumarin 7-O-glucosyltransferase, with broad substrate specificity from tobacco cultured cells." Plant Sci 157(1);105-112. PMID: 10940474

Taylor74: Taylor SS, Rigby PW, Hartley BS (1974). "Ribitol dehydrogenase from Klebsiella aerogenes. Purification and subunit structure." Biochem J 141(3);693-700. PMID: 4618776

Tsang79: Tsang Y-F, Ibrahim RK (1979). "Two forms of O-methyltransferase in tobacco cell suspension culture." Phytochemistry 18: 1131-1136.

Unnasch82: Unnasch TR, Brown GM (1982). "Purification and properties of dihydropterin oxidase from Drosophila melanogaster." J Biol Chem 257(23);14211-6. PMID: 6815189

Usui89: Usui S, Yu CA (1989). "Purification and properties of isopenicillin N epimerase from Streptomyces clavuligerus." Biochim Biophys Acta 999(1);78-85. PMID: 2804141

Wallenfels72: Wallenfels K, Weil R "beta-Galactosidase." Academic Press, NY 1972;617-663.

Wojciechowski75: Wojciechowski, ZdzisImageaw A. (1975). "Biosynthesis of oleanolic acid glycosides by subcellular fractions of Calendula officinalis seedlings." Phytochemistry. 14:1749-1753.


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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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