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MetaCyc Compound: dithiothreitol

Synonyms: dithiolthreitol, DTT, 1,4-Dithiothreitol, threo-1,4-Dimercapto-2,3-butanediol, 1,4-disulfanylbutane-2,3-diol, 1,4-Dithio-dl-threitol

Superclasses: an organosulfur compound a thiol

Chemical Formula: C4H10O2S2

Molecular Weight: 154.24 Daltons

Monoisotopic Molecular Weight: 154.0122209452 Daltons

SMILES: C(S)C(O)C(O)CS

InChI: InChI=1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4-/m0/s1

InChIKey: InChIKey=VHJLVAABSRFDPM-IMJSIDKUSA-N

Unification Links: CAS:3483-12-3 , ChEBI:42106 , ChemSpider:388336 , HMDB:HMDB13593 , KEGG:C00265 , MetaboLights:MTBLC42106 , PubChem:439196 , Wikipedia:Dithiothreitol

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 31.631197 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

glutathione-mediated detoxification II , sulfur volatiles biosynthesis :
a thiol + S-adenosyl-L-methionine → S-adenosyl-L-homocysteine + a methyl thioether + H+

sulfur oxidation IV (intracellular sulfur) :
intracellular S0n + a thiol → intracellular S0n-1 + a perthiol

thiosulfate disproportionation I (thiol-dependent) :
thiosulfate + 2 a thiol → sulfite + hydrogen sulfide + a disulfide + H+

Reactions known to produce the compound:

glutathione-mediated detoxification I , glutathione-mediated detoxification II :
an L-cysteine-S-conjugate + H2O → a thiol + pyruvate + ammonium

sulfur oxidation IV (intracellular sulfur) :
a perthiol + a [DsrE protein]-L-cysteine → a thiol + a [DsrE protein] persulfide

Not in pathways:
a thioglucoside + H2O → a sugar + a thiol
a ubiquitin C-terminal thioester + H2O → a ubiquitin + a thiol
a ubiquitin C-terminal thioester + H2O → a ubiquitin + a thiol

In Reactions of unknown directionality:

Not in pathways:
oxidized dithiothreitol + phylloquinone + H2O = dithiothreitol + vitamin K 2,3-epoxide
oxidized dithiothreitol + 3-hydroxy-2-methyl-3-phytyl-2,3-dihydronaphthoquinone + H2O = dithiothreitol + vitamin K 2,3-epoxide


3'-phosphoadenylyl-sulfate + a thiol = adenosine 3',5'-bisphosphate + S-alkyl thiosulfate
an L-cysteine-S-conjugate = a thiol + 2-aminoprop-2-enoate + H+

Enzymes activated by dithiothreitol, sorted by the type of activation, are:

Activator (Mechanism unknown) of: 3-demethylubiquinone-8 3-O-methyltransferase [Leppik76] , 3-octaprenyl-4-hydroxybenzoate carboxy-lyase [Leppik76a] , methylglyoxal reductase (NADPH-dependent) [Saikusa87] , tRNA C32 thiolase [Bouvier14] , sinapoyl-CoA: glucarolactone sinapoyltransferase [Strack87a] , dihydropterin oxidase [Unnasch82] , glycerophosphocholine cholinephosphodiesterase [Sugimori13] , phenylalanine 3-hydroxylase [Zhang11e] , potchoulol synthase [Munck90] , sequoyitol dehydrogenase [Ruis69] , carboxynorspermidine dehydrogenase [Nakao91] , CDP reductase [Roshick00] , 4-hydroxybenzaldehyde synthase [Sircar08] , 1-guanidino-1-deoxy-scyllo-inositol 4-phosphate phosphatase [Walker71] , cytidine 5'-monophosphate N-acetylneuraminate synthetase [RodriguezAparic92] , 3'-amino-3'-deoxyATP pyrophosphohydrolase [Espinosa99] , hydantoin racemase [Wiese00] , carboxynorspermidine decarboxylase [Nakao90] , oleanolate UDP-glucuronosyltransferase [Wojciechowski75] , deacetoxycephalosporin C hydroxylase [Baker91] , deacetoxycephalosporin C synthase [Dotzlaf89] , deacetoxycephalosporin C hydroxylase [Dotzlaf87] , deacetoxycephalosporin C synthase [Dotzlaf87, Baldwin87] , isopenicillin N synthase [Perry88] , isopenicillin N epimerase [Usui89] , L-gulono-γ-lactone oxidase [Nishikimi79] , 2-(2'-methylthio)ethylmalate synthase [Textor04] , alkenyl thiohydroximate-O-sulfate sulfohydrolase (epithionitrile-forming) [Burow06] , thiohydroximate-O-sulfate sulfohydrolase (nitrile-forming) [Burow06] , L-3-aminobutyryl coenzyme A deaminase [Jeng74] , galactinol synthase [Liu95c]

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

Inhibitor (Competitive) of: allantoinase [Mulrooney03] , ribitol dehydrogenase [Taylor74]

Inhibitor (Mechanism unknown) of: 2-amino-3-ketobutyrate CoA ligase [Mukherjee87] , ribonucleoside-triphosphate reductase [Eliasson92, Comment 1] , dihydrogeodin oxidase [Fujii87] , agmatine coumaroyltransferase [Burhenne03] , N-benzylformamide deformylase [Fukatsu04] , histidine decarboxylase [Guirard87] , geranylhydroquinone 3''-hydroxylase [Yamamoto00a] , δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine synthetase [Theilgaard97] , ethylnitronate monooxygenase [Gorlatova98] , ornithine carbamoyltransferase [Morizono97a] , acetyl-CoA:13-[O(2')-β-D-glucopyranosyl-β-D-glucopyranosyloxy]docosanoate acetyltransferase [Bucholtz76] , parathion hydrolase [Mulbry89] , sinapoylglucose:sinapoylglucose O-sinapoyltransferase [Dahlbender86] , violaxanthin de-epoxidase [Bugos96] , antheraxanthin de-epoxidase [Bugos96] , adenosine nucleosidase [Guranowski77] , ethylnitronate monooxygenase [Kido84]

Inhibitor (Other types) of: [heparan-sulfate]-6-O-sulfotransferase [Habuchi95] , phosphomannose isomerase [Shinabarger91] , GDP-D-mannose pyrophosphorylase [Shinabarger91]

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: nitric-oxide synthase , nitric oxide synthase , nitric-oxide synthase


References

Baker91: Baker BJ, Dotzlaf JE, Yeh WK (1991). "Deacetoxycephalosporin C hydroxylase of Streptomyces clavuligerus. Purification, characterization, bifunctionality, and evolutionary implication." J Biol Chem 266(8);5087-93. PMID: 2002049

Baldwin87: Baldwin JE, Adlington RM, Coates JB, Crabbe MJ, Crouch NP, Keeping JW, Knight GC, Schofield CJ, Ting HH, Vallejo CA (1987). "Purification and initial characterization of an enzyme with deacetoxycephalosporin C synthetase and hydroxylase activities." Biochem J 245(3);831-41. PMID: 3663194

Bouvier14: Bouvier D, Labessan N, Clemancey M, Latour JM, Ravanat JL, Fontecave M, Atta M (2014). "TtcA a new tRNA-thioltransferase with an Fe-S cluster." Nucleic Acids Res 42(12);7960-70. PMID: 24914049

Bucholtz76: Bucholtz ML, Light RJ (1976). "Acetylation of 13-sophorosyloxydocosanoic acid by an acetyltransferase purified from Candida bogoriensis." J Biol Chem 251(2);424-30. PMID: 1245481

Bugos96: Bugos RC, Yamamoto HY (1996). "Molecular cloning of violaxanthin de-epoxidase from romaine lettuce and expression in Escherichia coli." Proc Natl Acad Sci U S A 93(13);6320-5. PMID: 8692813

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

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.

Dotzlaf87: Dotzlaf JE, Yeh WK (1987). "Copurification and characterization of deacetoxycephalosporin C synthetase/hydroxylase from Cephalosporium acremonium." J Bacteriol 169(4);1611-8. PMID: 3558321

Dotzlaf89: Dotzlaf JE, Yeh WK (1989). "Purification and properties of deacetoxycephalosporin C synthase from recombinant Escherichia coli and its comparison with the native enzyme purified from Streptomyces clavuligerus." J Biol Chem 264(17);10219-27. PMID: 2656705

Eliasson92: Eliasson R, Pontis E, Fontecave M, Gerez C, Harder J, Jornvall H, Krook M, Reichard P (1992). "Characterization of components of the anaerobic ribonucleotide reductase system from Escherichia coli." J Biol Chem 267(35);25541-7. PMID: 1460049

Espinosa99: Espinosa JC, Tercero JA, Rubio MA, Jimenez A (1999). "The pur7 gene from the puromycin biosynthetic pur cluster of Streptomyces alboniger encodes a nudix hydrolase." J Bacteriol 181(16);4914-8. PMID: 10438762

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

Fukatsu04: Fukatsu H, Hashimoto Y, Goda M, Higashibata H, Kobayashi M (2004). "Amine-synthesizing enzyme N-substituted formamide deformylase: screening, purification, characterization, and gene cloning." Proc Natl Acad Sci U S A 101(38);13726-31. PMID: 15358859

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

Guirard87: Guirard BM, Snell EE (1987). "Purification and properties of pyridoxal-5'-phosphate-dependent histidine decarboxylases from Klebsiella planticola and Enterobacter aerogenes." J Bacteriol 169(9);3963-8. PMID: 3114230

Guranowski77: Guranowski A, Schneider Z (1977). "Purification and characterization of adenosine nucleosidase from barley leaves." Biochim Biophys Acta 482(1);145-58. PMID: 861230

Habuchi95: Habuchi H, Habuchi O, Kimata K (1995). "Purification and characterization of heparan sulfate 6-sulfotransferase from the culture medium of Chinese hamster ovary cells." J Biol Chem 270(8);4172-9. PMID: 7876170

Jeng74: Jeng I, Barker HA (1974). "Purification and properties of l-3-aminobutyryl coenzyme A deaminase from a lysine-fermenting Clostridium." J Biol Chem 249(20);6578-84. PMID: 4420467

Kido84: Kido T, Soda K (1984). "Oxidation of anionic nitroalkanes by flavoenzymes, and participation of superoxide anion in the catalysis." Arch Biochem Biophys 234(2);468-75. PMID: 6149727

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

Leppik76: Leppik RA, Stroobant P, Shineberg B, Young IG, Gibson F (1976). "Membrane-associated reactions in ubiquinone biosynthesis. 2-Octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone methyltransferase." Biochim Biophys Acta 1976;428(1);146-56. PMID: 769831

Leppik76a: Leppik RA, Young IG, Gibson F (1976). "Membrane-associated reactions in ubiquinone biosynthesis in Escherichia coli. 3-Octaprenyl-4-hydroxybenzoate carboxy-lyase." Biochim Biophys Acta 1976;436(4);800-10. PMID: 782527

Liu95c: Liu JJ, Odegard W, de Lumen BO (1995). "Galactinol synthase from kidney bean cotyledon and zucchini leaf. Purification and N-terminal sequences." Plant Physiol 109(2);505-11. PMID: 7480343

Morizono97a: 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

Mukherjee87: Mukherjee JJ, Dekker EE (1987). "Purification, properties, and N-terminal amino acid sequence of homogeneous Escherichia coli 2-amino-3-ketobutyrate CoA ligase, a pyridoxal phosphate-dependent enzyme." J Biol Chem 1987;262(30);14441-7. PMID: 3117785

Mulbry89: Mulbry WW, Karns JS (1989). "Purification and characterization of three parathion hydrolases from gram-negative bacterial strains." Appl Environ Microbiol 55(2);289-93. PMID: 2541658

Mulrooney03: Mulrooney SB, Hausinger RP (2003). "Metal ion dependence of recombinant Escherichia coli allantoinase." J Bacteriol 185(1);126-34. PMID: 12486048

Munck90: Munck SL, Croteau R (1990). "Purification and characterization of the sesquiterpene cyclase patchoulol synthase from Pogostemon cablin." Arch Biochem Biophys 282(1);58-64. PMID: 2171435

Nakao90: Nakao H, Shinoda S, Yamamoto S (1990). "Purification and properties of carboxynorspermidine decarboxylase, a novel enzyme involved in norspermidine biosynthesis, from Vibrio alginolyticus." Journal of General Microbiology 136, 1699-1704.

Nakao91: Nakao H, Shinoda S, Yamamoto S (1991). "Purification and some properties of carboxynorspermidine synthase participating in a novel biosynthetic pathway for norspermidine in Vibrio alginolyticus." J Gen Microbiol 137(7);1737-42. PMID: 1955861

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

Perry88: Perry D, Abraham EP, Baldwin JE (1988). "Factors affecting the isopenicillin N synthetase reaction." Biochem J 255(1);345-51. PMID: 3143358

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

Roshick00: Roshick C, Iliffe-Lee ER, McClarty G (2000). "Cloning and characterization of ribonucleotide reductase from Chlamydia trachomatis." J Biol Chem 275(48);38111-9. PMID: 10984489

Ruis69: Ruis H, Hoffmann-Ostenhof O (1969). "Enzymic epimerization of sequoyitol to D-pinitol in Trifolium incarnatum." Eur J Biochem 7(3);442-8. PMID: 4389340

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.

Shinabarger91: Shinabarger D, Berry A, May TB, Rothmel R, Fialho A, Chakrabarty AM (1991). "Purification and characterization of phosphomannose isomerase-guanosine diphospho-D-mannose pyrophosphorylase. A bifunctional enzyme in the alginate biosynthetic pathway of Pseudomonas aeruginosa." J Biol Chem 266(4);2080-8. PMID: 1846611

Sircar08: Sircar D, Mitra A (2008). "Evidence for p-hydroxybenzoate formation involving enzymatic phenylpropanoid side-chain cleavage in hairy roots of Daucus carota." J Plant Physiol 165(4);407-14. PMID: 17658659

Strack87a: Strack D, Keller H, Weissenbock G (1987). "Enzymatic synthesis of hydroxycinnamic acid esters of sugar acids and hydroaromatic acids by protein preparations from rye (Secale cereale) primary leaves." Journal of Plant Physiology 131:61-73.

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

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

Textor04: Textor S, Bartram S, Kroymann J, Falk KL, Hick A, Pickett JA, Gershenzon J (2004). "Biosynthesis of methionine-derived glucosinolates in Arabidopsis thaliana: recombinant expression and characterization of methylthioalkylmalate synthase, the condensing enzyme of the chain-elongation cycle." Planta 218(6);1026-35. PMID: 14740211

Theilgaard97: Theilgaard HB, Kristiansen KN, Henriksen CM, Nielsen J (1997). "Purification and characterization of delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine synthetase from Penicillium chrysogenum." Biochem J 327 ( Pt 1);185-91. PMID: 9355751

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

Walker71: Walker MS, Walker JB (1971). "Streptomycin biosynthesis. Separation and substrate specificities of phosphatases acting on guanidinodeoxy-scyllo-inositol phosphate and streptomycin-(streptidino)phosphate." J Biol Chem 246(22);7034-40. PMID: 4331203

Wiese00: Wiese A, Pietzsch M, Syldatk C, Mattes R, Altenbuchner J (2000). "Hydantoin racemase from Arthrobacter aurescens DSM 3747: heterologous expression, purification and characterization." J Biotechnol 80(3);217-30. PMID: 10949312

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

Yamamoto00a: Yamamoto H, Inoue K, Li SM, Heide L (2000). "Geranylhydroquinone 3"-hydroxylase, a cytochrome P-450 monooxygenase from Lithospermum erythrorhizon cell suspension cultures." Planta 210(2);312-7. PMID: 10664138

Zhang11e: Zhang W, Ames BD, Walsh CT (2011). "Identification of phenylalanine 3-hydroxylase for meta-tyrosine biosynthesis." Biochemistry 50(24);5401-3. PMID: 21615132


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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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