Topaquinone

Topaquinone
Names
	IUPAC name (2S)-2-Amino-3-(4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)propanoic acid
	Other names 6-Hydroxydopaquinone
Identifiers
CAS Number	64192-68-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:36076;
ChemSpider	110408;
DrugBank	DB04334;
PubChem CID	123871;
UNII	PAG3GKA51Y;
CompTox Dashboard (EPA)	DTXSID40982735 ;
	InChI InChI=1S/C9H9NO5/c10-5(9(14)15)1-4-2-7(12)8(13)3-6(4)11/h2-3,5,11H,1,10H2,(H,14,15)/t5-/m0/s1 Key: YWRFBISQAMHSIX-YFKPBYRVSA-N;
	SMILES C1=C(C(=CC(=O)C1=O)O)C[C@@H](C(=O)O)N;
Properties
Chemical formula	C9H9NO5
Molar mass	211.173 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Topaquinone (TPQ) is a redox cofactor derived from the amino acid tyrosine. Its name derives from 2,4,5-trihydroxyphenylalanine-quinone. Its structure was first identified in 1990.^[1] It is used by copper amine oxidases which contain a tyrosine residue near the active site. This residue catalyses its own transition, first to dopaquinone and then to topaquinone, in a Cu²⁺ dependent manner.^[1]

References

^ ^a ^b Dooley, D. M. (Feb 1999). "Structure and biogenesis of topaquinone and related cofactors". Journal of Biological Inorganic Chemistry. 4 (1): 1–11. doi:10.1007/s007750050283. ISSN 0949-8257. PMID 10499097. S2CID 10104769.

[Dooley-1] Dooley, D. M. (Feb 1999). "Structure and biogenesis of topaquinone and related cofactors". Journal of Biological Inorganic Chemistry. 4 (1): 1–11. doi:10.1007/s007750050283. ISSN 0949-8257. PMID 10499097. S2CID 10104769.

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