Tryptophan tryptophylquinone

Tryptophan tryptophylquinone
Names

IUPAC name 2-amino-3-[2-[2-amino-3-(2-carboxyethyl)-6,7-dioxo-1H-indol-4-yl]-1H-indol-3-yl]propanoic acid
Identifiers
CAS Number	134645-25-3^Y
3D model (Jmol)	Interactive image
MeSH	Tryptophan+tryptophylquinone
PubChem	5486829
SMILES C1=CC=C2C(=C1)C(=C(N2)C3=CC(=O)C(=O)C4=C3C(=C(N4)N)CCC(=O)O)CC(C(=O)O)N
Properties
Chemical formula	C₂₂H₂₀N₄O₆
Molar mass	436.419
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

Tryptophan tryptophylquinone(TTQ) is an enzyme cofactor, generated by posttranslational modification of amino acids within the protein. Methylamine dehydrogenase (MADH), an amine dehydrogenase, requires TTQ for its catalytic function.^[1]

Serine/Threonine	Phosphorylation Dephosphorylation Glycosylation Methylidene-imidazolone (MIO) formation

Tyrosine	Phosphorylation Dephosphorylation Sulfation Porphyrin ring linkage Adenylylation Flavin linkage Topaquinone (TPQ) formation Detyrosination

Cysteine	Palmitoylation Prenylation

Aspartate	Succinimide formation

Glutamate	Carboxylation Methylation Polyglutamylation Polyglycylation

Asparagine	Deamidation Glycosylation

Glutamine	Transglutamination

Lysine	Methylation Acetylation Acylation Adenylylation Hydroxylation Ubiquitination Sumoylation ADP-ribosylation Deamination Oxidative deamination to aldehyde O-glycosylation Imine formation Glycation Carbamylation Succinylation

Arginine	Citrullination Methylation ADP-ribosylation

Proline	Hydroxylation

Histidine	Diphthamide formation Adenylylation

Tryptophan	C-mannosylation

Crosslinks between two AAs

Cysteine-Cysteine	Disulfide bond

Methionine-Hydroxylysine	Sulfilimine bond

Lysine-Tyrosylquinone	Lysine tyrosylquinone (LTQ) formation

Tryptophan-Tryptophylquinone	Tryptophan tryptophylquinone (TTQ) formation

Three consecutive AAs
(chromophore formation)

Serine–Tyrosine–Glycine	p-Hydroxybenzylidene-imidazolinone formation

Histidine–Tyrosine–Glycine	4-(p-hydroxybenzylidene)-5-imidazolinone formation

Crosslinks between four AAs

Allysine-Allysine-Allysine-Lysine	Desmosine

References

↑ Davidson VL, Liu A: Uncovering novel biochemistry in the mechanism of tryptophan tryptophylquinone cofactor biosynthesis Curr. Op. Chem. Biol. 2009, 13: 469-474

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