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 (JSmol)	Interactive image
MeSH	Tryptophan+tryptophylquinone
PubChem CID	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	436.424 g·mol⁻¹
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

Chemical compound

Tryptophan tryptophylquinone (TTQ)^[1] 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.^[2]

References

^ Davidson, V. L.; Liu, A. (2012). "Tryptophan tryptophylquinone biosynthesis: A radical approach to posttranslational modification, by Victor L. Davidson1 and Aimin Liu2, on National Center for Biotechnology Information, U.S. National Library of Medicine, published 2012 Jan 28. doi: 10.1016/j.bbapap.2012.01.008". Biochimica et Biophysica Acta. 1824 (11): 1299–1305. doi:10.1016/j.bbapap.2012.01.008. PMC 3432176. PMID 22314272.
^ Davidson VL, Liu A (2009). "Uncovering novel biochemistry in the mechanism of tryptophan tryptophylquinone cofactor biosynthesis". Curr. Opin. Chem. Biol. 13 (4): 469–474. doi:10.1016/j.cbpa.2009.06.026. PMC 2749888. PMID 19648051.

Protein primary structure and posttranslational modifications

General

Peptide bond
Protein biosynthesis
Proteolysis
Racemization
N–O acyl shift

N terminus

C terminus

Single specific AAs

Serine/Threonine	Phosphorylation Dephosphorylation Glycosylation O-GlcNAc ADP-ribosylation
Tyrosine	Phosphorylation Dephosphorylation ADP-ribosylation Sulfation Porphyrin ring linkage Adenylylation Flavin linkage Topaquinone (TPQ) formation Detyrosination
Cysteine	Palmitoylation Prenylation
Aspartate	Succinimide formation ADP-ribosylation
Glutamate	Carboxylation ADP-ribosylation 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 Lactylation Propionylation Butyrylation
Arginine	Citrullination Methylation ADP-ribosylation
Proline	Hydroxylation
Histidine	Diphthamide formation Adenylylation
Tryptophan	C-mannosylation

Crosslinks between two AAs

Cysteine–Cysteine	Disulfide bond ADP-ribosylation
Methionine–Hydroxylysine	Sulfilimine bond
Lysine–Tyrosine	Lysine tyrosylquinone (LTQ) formation
Tryptophan–Tryptophan	Tryptophan tryptophylquinone (TTQ) formation

Crosslinks between three AAs

Serine–Tyrosine–Glycine	p-Hydroxybenzylidene-imidazolinone (HBI) formation (chromophore)
Histidine–Tyrosine–Glycine	4-(p-hydroxybenzylidene)-5-imidazolinone (HBI) formation (chromophore)
Alanine–Serine–Glycine	Methylidene-imidazolone (MIO) formation