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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 acid all carboxy acids a carboxylate an amino acid a basic amino acid
an acid all carboxy acids a carboxylate an amino acid a polar amino acid a positively-charged polar amino acid
an acid all carboxy acids a carboxylate an amino acid an alpha amino acid a standard alpha amino acid
an acid all carboxy acids a carboxylate an amino acid an aromatic amino acid an aromatic L-amino acid
an acid all carboxy acids a carboxylate an amino acid an L-amino acid an aromatic L-amino acid
an acid all carboxy acids a carboxylate an amino acid an L-amino acid
an amino acid or its derivative an amino acid a basic amino acid
an amino acid or its derivative an amino acid a polar amino acid a positively-charged polar amino acid
an amino acid or its derivative an amino acid an alpha amino acid a standard alpha amino acid
an amino acid or its derivative an amino acid an aromatic amino acid an aromatic L-amino acid
an amino acid or its derivative an amino acid an L-amino acid an aromatic L-amino acid
an amino acid or its derivative an amino acid an L-amino acid

Chemical Formula: C6H9N3O2

Molecular Weight: 155.16 Daltons

Monoisotopic Molecular Weight: 155.0694765487 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:
L-methionine + a 2-oxo carboxylate = 2-oxo-4-methylthiobutanoate + a standard α amino acid

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

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

In Transport reactions:
ATP + L-histidine[periplasmic space] + H2O → ADP + L-histidine[cytosol] + phosphate + H+ ,
an aromatic amino acid[cytosol]an aromatic amino acid[periplasmic 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
Page generated by SRI International Pathway Tools version 19.0 on Sat Aug 29, 2015, biocyc12.