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discounted EARLY registration ends Dec 31, 2014
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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:
phylloquinone + oxidized dithiothreitol + 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 [Strack87] , dihydropterin oxidase [Unnasch82] , glycerophosphocholine cholinephosphodiesterase [Sugimori13] , phenylalanine 3-hydroxylase [Zhang11c] , 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 [Liu95b]

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 [Yamamoto00] , δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine synthetase [Theilgaard97] , ethylnitronate monooxygenase [Gorlatova98] , ornithine carbamoyltransferase [Morizono97] , 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

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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

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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

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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

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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

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Zhang11c: 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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