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

Abbrev Name: tyr

Synonyms: Y, tyr, tyrosine, L-tyr

Superclasses: an acid all carboxy acids a carboxylate an amino acid a polar amino acid an uncharged 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 polar amino acid an uncharged 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

Component of: TyrR-Tyrosine DNA-binding transcriptional repressor

Chemical Formula: C9H11NO3

Molecular Weight: 181.19 Daltons

Monoisotopic Molecular Weight: 181.0738932246 Daltons

L-tyrosine compound structure

SMILES: C(C(CC1(C=CC(O)=CC=1))[N+])(=O)[O-]

InChI: InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1

InChIKey: InChIKey=OUYCCCASQSFEME-QMMMGPOBSA-N

Unification Links: CAS:60-18-4 , ChEBI:58315 , HMDB:HMDB00158 , IAF1260:33785 , KEGG:C00082 , MetaboLights:MTBLC58315 , PubChem:6942100

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -88.6

Reactions known to consume the compound:

thiazole biosynthesis I (E. coli) :
L-tyrosine + S-adenosyl-L-methionine + NADPH → 2-iminoacetate + 4-methylphenol + 5'-deoxyadenosine + L-methionine + NADP+ + H+

tRNA charging :
a tRNAtyr + L-tyrosine + ATP + H+ → an L-tyrosyl-[tRNAtyr] + AMP + diphosphate

Reactions known to produce the compound:

Not in pathways:
O-phospho-L-tyrosine[periplasmic space] + H2O[periplasmic space]L-tyrosine[periplasmic space] + phosphate[periplasmic space]

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-tyrosine biosynthesis I :
L-tyrosine + 2-oxoglutarate ↔ 4-hydroxyphenylpyruvate + L-glutamate

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

In Reactions of unknown directionality:

Not in pathways:
TyrR + L-tyrosine = TyrR-tyr

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:
L-tyrosine[periplasmic space] + H+[periplasmic space]L-tyrosine[cytosol] + H+[cytosol] ,
an aromatic amino acid[cytosol]an aromatic amino acid[periplasmic space]

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

Inhibitor (Competitive) of: prephenate dehydrogenase [Hudson83] , 2-dehydro-3-deoxyphosphoheptonate aldolase [Schoner76]

Inhibitor (Mechanism unknown) of: chorismate mutase [Hudson83] , phenylalanine aminotransferase [Collier72] , leucine aminotransferase [Collier72] , tyrosine aminotransferase [Collier72]

In Growth Media: Neidhardt EZ rich defined medium , PMA nitrogen source test + tyr

Transcription Units regulated by related protein TyrR-Tyrosine DNA-binding transcriptional repressor (8 total):

Transcription-unit diagram

Transcription-unit diagram

Transcription-unit diagram

Transcription-unit diagram

Transcription-unit diagram

Transcription-unit diagram

Transcription-unit diagram

Transcription-unit diagram


References

Collier72: Collier RH, Kohlhaw G (1972). "Nonidentity of the aspartate and the aromatic aminotransferase components of transaminase A in Escherichia coli." J Bacteriol 1972;112(1);365-71. PMID: 4404056

Hudson83: Hudson GS, Howlett GJ, Davidson BE (1983). "The binding of tyrosine and NAD+ to chorismate mutase/prephenate dehydrogenase from Escherichia coli K12 and the effects of these ligands on the activity and self-association of the enzyme. Analysis in terms of a model." J Biol Chem 1983;258(5);3114-20. PMID: 6338013

Schoner76: Schoner R, Herrmann KM (1976). "3-Deoxy-D-arabino-heptulosonate 7-phosphate synthase. Purification, properties, and kinetics of the tyrosine-sensitive isoenzyme from Escherichia coli." J Biol Chem 1976;251(18);5440-7. PMID: 9387


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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 Fri Aug 28, 2015, biocyc13.