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MetaCyc Compound: lysine tyrosylquinone

Synonyms: LTQ

Superclasses: an aldehyde or ketone a ketone a cyclic ketone a quinone

Summary:
Lysine tyrosylquinone (LTQ) has been identified as the active site cofactor in lysyl oxidase [Wang97a, Mure03].

lysine tyrosylquinone compound structure

SMILES: C(=O)([R2])C(N[R1])CCCCNC1(=CC(=[O-])C(=O)C=C(CC(N[R3])C(=O)[R4])1)

Unification Links: ChEBI:20489

Reactions known to consume the compound:

phenylacetate degradation II (anaerobic) :
phenylacetyl-CoA + 2 a quinone + H2O → 2 a quinol + phenylglyoxylyl-CoA

quinate degradation I :
L-quinate + a quinone → 3-dehydroquinate + a quinol

shikimate degradation I :
shikimate + a quinone → 3-dehydroshikimate + a quinol

thiosulfate oxidation II (via tetrathionate) :
2 thiosulfate + a quinone → tetrathionate + a quinol

Not in pathways:
a cyclic alcohol + a quinonea cyclic ketone + a quinol

Not in pathways:
a cyclic alcohol + a quinonea cyclic ketone + a quinol

Reactions known to produce the compound:

cuticular wax biosynthesis :
a secondary alcohol + an oxidized unknown electron acceptor → a ketone + an reduced unknown electron acceptor

Not in pathways:
a secondary alcohol + oxygen → a ketone + hydrogen peroxide

Not in pathways:
a nitroalkane + oxygen + H2O → an aldehyde or ketone + nitrite + hydrogen peroxide + H+

Reactions known to both consume and produce the compound:

Not in pathways:
2 a quinone + NADPH + H+ ↔ 2 a semiquinone + NADP+

In Reactions of unknown directionality:

Not in pathways:
2 a quinone + NADH + H+ = 2 a semiquinone + NAD+
1-(β-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone + H+ = a quinol + 1-(β-D ribofuranosyl)nicotinamide

Not in pathways:
a ketone + NADP+ = an enone + NADPH + H+
a secondary alcohol + an oxidized coenzyme F420 = a ketone + a reduced coenzyme F420
a secondary alcohol + NADP+ = a ketone + NADPH + H+
a secondary alcohol + NAD+ = a ketone + NADH + H+

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: putrescine oxidase

Credits:
Created 21-Jan-2010 by Caspi R , SRI International


References

Mure03: Mure M, Wang SX, Klinman JP (2003). "Synthesis and characterization of model compounds of the lysine tyrosyl quinone cofactor of lysyl oxidase." J Am Chem Soc 125(20);6113-25. PMID: 12785842

Wang97a: Wang SX, Nakamura N, Mure M, Klinman JP, Sanders-Loehr J (1997). "Characterization of the native lysine tyrosylquinone cofactor in lysyl oxidase by Raman spectroscopy." J Biol Chem 272(46);28841-4. PMID: 9360949


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Fri Aug 28, 2015, biocyc14.