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Escherichia coli K-12 substr. MG1655 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

dithiothreitol compound structure

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): -71.08

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

Activator (Mechanism unknown) of: 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 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 , methionine sulfoxide reductase , 2'-deoxycytidine diphosphate:oxidized NrdH glutaredoxin-like protein oxidoreductase


References

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

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. 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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