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Escherichia coli K-12 substr. MG1655 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 Formation (ΔfG in kcal/mol): -71.08

In Transport reactions:
an organosulfur compound[periplasm]an organosulfur compound[extracellular space]

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

Activator (Mechanism unknown) of: fructose-1,6-bisphosphatase [Brown09], L-cystine ABC transporter [Deutch14], tRNA C32 thiolase [Bouvier14], methylglyoxal reductase (NADPH-dependent) [Saikusa87], 3-octaprenyl-4-hydroxybenzoate carboxy-lyase [Leppik76], 3-demethylubiquinone-8 3-O-methyltransferase [Leppik76a]

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

Inhibitor (Competitive) of: allantoinase [Mulrooney03] Inhibitor (Mechanism unknown) of: ribonucleoside-triphosphate reductase [Eliasson92, Comment 1], 2-amino-3-ketobutyrate CoA ligase [Mukherjee87]

This compound has been characterized as an alternative substrate of the following enzymes: thiosulfate sulfurtransferase, 2'-deoxycytidine diphosphate:oxidized NrdH glutaredoxin-like protein oxidoreductase, methionine sulfoxide reductase


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. PMID: 24914049

Brown09: Brown G, Singer A, Lunin VV, Proudfoot M, Skarina T, Flick R, Kochinyan S, Sanishvili R, Joachimiak A, Edwards AM, Savchenko A, Yakunin AF (2009). "Structural and biochemical characterization of the type II fructose-1,6-bisphosphatase GlpX from Escherichia coli." J Biol Chem 284(6);3784-92. PMID: 19073594

Deutch14: Deutch CE, Spahija I, Wagner CE (2014). "Susceptibility of Escherichia coli to the toxic L-proline analogue L-selenaproline is dependent on two L-cystine transport systems." J Appl Microbiol 117(5);1487-99. PMID: 25139244

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

Leppik76: 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

Leppik76a: 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

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

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

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.

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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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