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Escherichia coli K-12 substr. MG1655 Compound: L-leucine

Abbrev Name: leu

Synonyms: (2S)-α-2-amino-4-methylvaleric acid, L, leu, leucine, 2-amino-4-methylvaleric acid, (2S)-α-leucine, L-leu

Superclasses: an acidall carboxy acidsa carboxylatean amino acida neutral amino acid
an acidall carboxy acidsa carboxylatean amino acida non-polar amino acid
an acidall carboxy acidsa carboxylatean amino acidan alpha amino acida branched-chain amino acid
an acidall carboxy acidsa carboxylatean amino acidan alpha amino acida standard alpha amino acid
an acidall carboxy acidsa carboxylatean amino acidan L-amino acid
an amino acid or its derivativean amino acida neutral amino acid
an amino acid or its derivativean amino acida non-polar amino acid
an amino acid or its derivativean amino acidan alpha amino acida branched-chain amino acid
an amino acid or its derivativean amino acidan alpha amino acida standard alpha amino acid
an amino acid or its derivativean amino acidan L-amino acid


Component of: Lrp-Leucine DNA-binding transcriptional dual regulator (extended summary available)

Chemical Formula: C6H13NO2

Molecular Weight: 131.17 Daltons

Monoisotopic Molecular Weight: 132.10245369880002 Daltons

L-leucine compound structure

SMILES: CC(C)CC([N+])C([O-])=O

InChI: InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1

InChIKey: InChIKey=ROHFNLRQFUQHCH-YFKPBYRVSA-N

Unification Links: CAS:61-90-5, ChEBI:57427, HMDB:HMDB00687, IAF1260:33942, KEGG:C00123, MetaboLights:MTBLC57427, NCI:46709, PubChem:7045798

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -84.2

Reactions known to consume the compound:

tRNA charging :
a tRNAleu + L-leucine + ATP + H+ → an L-leucyl-[tRNAleu] + AMP + diphosphate

Reactions known to produce the compound:

Not in pathways:
L-alanyl-L-leucine + H2O → L-alanine + L-leucine

Not in pathways:
a peptide with an N-terminal X-L-proline + H2O → a standard α amino acid + a peptide with an N-terminal L-proline + H+
a peptide + H2O → a standard α amino acid + a peptide
a protein + H2O → a peptide + a standard α amino acid
a protein + H2O → a peptide + a standard α amino acid
a protein + H2O → a standard α amino acid + a peptide
β-aspartyl dipeptide + H2O → L-aspartate + a standard α amino acid
a dipetide with an N-terminal L-aspartate + H2O → L-aspartate + a standard α amino acid
a tripeptide + H2O → a dipeptide + a standard α amino acid
a dipeptide with proline at the C-terminal + H2O → L-proline + a standard α amino acid
a dipeptide + H2O → 2 a standard α amino acid

Not in pathways:
a polypeptide + H2O → a polypeptide + an L-amino acid

Not in pathways:
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
a 1-acyl 2-lyso-phosphatidylcholine + H2O → a carboxylate + sn-glycero-3-phosphocholine + H+

Reactions known to both consume and produce the compound:

L-leucine biosynthesis :
L-leucine + 2-oxoglutarate ↔ 4-methyl-2-oxopentanoate + L-glutamate

In Reactions of unknown directionality:

Not in pathways:
Lrp + L-leucine = Lrp-leu

Not in pathways:
L-methionine + a 2-oxo carboxylate = 2-oxo-4-methylthiobutanoate + a standard α amino acid

Not in pathways:
a 5-L-glutamyl-[peptide][periplasm] + an amino acid[periplasm] = a 5-L-glutamyl-amino acid[periplasm] + a peptide[periplasm]

Not in pathways:
a 2-acyl 1-lyso-phosphatidylcholine + H2O = a carboxylate + sn-glycero-3-phosphocholine + H+
an aldehyde[periplasm] + FAD[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + FADH2[periplasm]

In Transport reactions:
ATP + L-leucine[periplasm] + H2O → ADP + L-leucine[cytosol] + phosphate + H+,
Na+[periplasm] + L-leucine[periplasm] → Na+[cytosol] + L-leucine[cytosol],
L-leucine[cytosol] + H+[periplasm]L-leucine[periplasm] + H+[cytosol],
an amino acid[periplasm]an amino acid[extracellular space]

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

Inhibitor (Mechanism unknown) of: threonine deaminase [Vonder72], aspartate kinase [Huang93], acetolactate synthase [Gollop83], acetohydroxybutanoate synthase, acetohydroxybutanoate synthase [Gollop83], phenylalanine aminotransferase [Powell78a], leucine aminotransferase [Powell78a], acetolactate synthase, tyrosine aminotransferase [Powell78a], 2-isopropylmalate synthase [Stieglitz74]

In Growth Media: Neidhardt EZ rich defined medium, Davis and Mingioli medium A, PMA nitrogen source test + leu, PMA carbon source test + leu, M56 medium

Transcription Units regulated by related protein Lrp-Leucine DNA-binding transcriptional dual regulator (23 total):

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References

Gollop83: Gollop N, Chipman DM, Barak Z (1983). "Inhibition of acetohydroxy acid synthase by leucine." Biochim Biophys Acta 1983;748(1);34-9. PMID: 6351926

Huang93: Huang KJ, Hseu TH (1993). "Effects of lysine-sensitive aspartokinase III on lysine biosynthesis in Escherichia coli K-12." Proc Natl Sci Counc Repub China B 17(3);91-7. PMID: 8290655

Powell78a: Powell JT, Morrison JF (1978). "Role of the Escherichia coli aromatic amino acid aminotransferase in leucine biosynthesis." J Bacteriol 136(1);1-4. PMID: 361681

Stieglitz74: Stieglitz BI, Calvo JM (1974). "Distribution of the isopropylmalate pathway to leucine among diverse bacteria." J Bacteriol 118(3);935-41. PMID: 4829932

Vonder72: Vonder Haar RA, Umbarger HE (1972). "Isoleucine and valine metabolism in Escherichia coli. XIX. Inhibition of isoleucine biosynthesis by glycyl-leucine." J Bacteriol 112(1);142-7. PMID: 4562390


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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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