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MetaCyc Compound: L-dithiothreitol

Synonyms: L-DTT, L-threo-1,4-dimercapto-2,3-butanediol, L-1,4-disulfanylbutane-2,3-diol, L-1,4-dithiothreitol

Superclasses: an organosulfur compounda thiol

Chemical Formula: C4H10O2S2

Molecular Weight: 154.24 Daltons

Monoisotopic Molecular Weight: 154.0122209452 Daltons

L-dithiothreitol compound structure


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


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): 31.631197Inferred 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+

Not in pathways:
a [sulfatase]-L-cysteine + 2 a thiol + oxygen → a [sulfatase]-3-oxo-L-alanine + hydrogen sulfide + a disulfide + H2O

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 [Rhd protein]-L-cysteine → a thiol + a [Rhd protein] persulfide

Not in pathways:
a thioglucoside + H2O → a sugar + a thiol

In Reactions of unknown directionality:

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

Not in pathways:
3'-phosphoadenylyl-sulfate + a thiol = an S-alkyl thiosulfate + adenosine 3',5'-bisphosphate
an L-cysteine-S-conjugate = a thiol + 2-aminoprop-2-enoate + H+

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

Activator (Mechanism unknown) of: 3-demethylubiquinone-8 3-O-methyltransferase [Leppik76a], 3-octaprenyl-4-hydroxybenzoate carboxy-lyase [Leppik76], fructose-1,6-bisphosphatase [Brown09], methylglyoxal reductase (NADPH-dependent) [Saikusa87], tRNA C32 thiolase [Bouvier14], L-cystine ABC transporter [Deutch14], sinapoyl-CoA: glucarolactone sinapoyltransferase [Strack87], dihydropterin oxidase [Unnasch82], glycerophosphocholine cholinephosphodiesterase [Sugimori13], phenylalanine 3-hydroxylase [Zhang11a], 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 [Jeng74a], galactinol synthase [Liu95]

Enzymes inhibited by L-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 [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 [Guranowski77a], 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

This compound has been characterized as an alternative substrate of the following enzymes: methionine sulfoxide reductase, thiosulfate sulfurtransferase, 2'-deoxycytidine diphosphate:oxidized NrdH glutaredoxin-like protein oxidoreductase, β-cyano-L-alanine synthase, thiobenzoate-S-methyltransferase


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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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