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

Abbrev Name: his

Synonyms: glyoxaline-5-alanine, α-amino-4-imidazoleproprionic acid, (S)-α-amino-1H-imidazole-4-propanoic acid, H, histidine, his, L-his

Superclasses: an acidall carboxy acidsa carboxylatean amino acida basic amino acid
an acidall carboxy acidsa carboxylatean amino acida polar amino acida positively-charged polar amino acid
an acidall carboxy acidsa carboxylatean amino acidan alpha amino acida standard alpha amino acid
an acidall carboxy acidsa carboxylatean amino acidan aromatic amino acidan aromatic L-amino acid
an acidall carboxy acidsa carboxylatean amino acidan L-amino acidan aromatic L-amino acid
an acidall carboxy acidsa carboxylatean amino acidan L-amino acid
an amino acid or its derivativean amino acida basic amino acid
an amino acid or its derivativean amino acida polar amino acida positively-charged polar 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 aromatic amino acidan aromatic L-amino acid
an amino acid or its derivativean amino acidan L-amino acidan aromatic L-amino acid
an amino acid or its derivativean amino acidan L-amino acid


Chemical Formula: C6H9N3O2

Molecular Weight: 155.16 Daltons

Monoisotopic Molecular Weight: 156.0773015808 Daltons

L-histidine compound structure

SMILES: C1(NC=NC=1CC(C(=O)[O-])[N+])

InChI: InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1

InChIKey: InChIKey=HNDVDQJCIGZPNO-YFKPBYRVSA-N

Unification Links: CAS:71-00-1, ChEBI:57595, HMDB:HMDB00177, IAF1260:33985, KEGG:C00135, MetaboLights:MTBLC57595, PubChem:6971009

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -57.44

Reactions known to consume the compound:

tRNA charging :
a tRNAhis + L-histidine + ATP + H+ → an L-histidyl-[tRNAhis] + AMP + diphosphate

Reactions known to produce the compound:

L-histidine biosynthesis :
histidinal + NAD+ + H2O → L-histidine + NADH + 2 H+

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

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:

Not in pathways:
an aromatic amino acid + 2-oxoglutarate ↔ an aromatic oxo-acid + L-glutamate

In Reactions of unknown directionality:

Not in pathways:
histidinol + 2 NAD+ + H2O = L-histidine + 2 NADH + 3 H+

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-histidine[periplasm] + H2O → ADP + L-histidine[cytosol] + phosphate + H+,
an aromatic amino acid[cytosol]an aromatic amino acid[periplasm],
an amino acid[periplasm]an amino acid[extracellular space]

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

Inhibitor (Competitive) of: histidinol-phosphatase [Brady73] Inhibitor (Allosteric) of: ATP phosphoribosyltransferase [Tebar76] Inhibitor (Mechanism unknown) of: glutamine synthetase [Woolfolk67, Bender77, Comment 1]

This compound has been characterized as an alternative substrate of the following enzymes: leucine efflux transporter, methionine-oxo-acid transaminase

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


References

Bender77: Bender RA, Janssen KA, Resnick AD, Blumenberg M, Foor F, Magasanik B (1977). "Biochemical parameters of glutamine synthetase from Klebsiella aerogenes." J Bacteriol 129(2);1001-9. PMID: 14104

Brady73: Brady DR, Houston LL (1973). "Some properties of the catalytic sites of imidazoleglycerol phosphate dehydratase-histidinol phosphate phosphatase, a bifunctional enzyme from Salmonella typhimurium." J Biol Chem 1973;248(7);2588-92. PMID: 4349042

Tebar76: Tebar AR, Ballesteros AO (1976). "Kinetic properties of ATP phosphoribosyltransferase of Escherichia coli." Mol Cell Biochem 11(3);131-6. PMID: 781521

Woolfolk67: Woolfolk CA, Stadtman ER (1967). "Regulation of glutamine synthetase. 3. Cumulative feedback inhibition of glutamine synthetase from Escherichia coli." Arch Biochem Biophys 118(3);736-55. PMID: 4860415


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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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