Tiglyl-CoA : Wikipedia, the free encyclopedia

Tiglyl-CoA

Tiglyl-CoA
Names

IUPAC name 3′-O-Phosphonoadenosine 5′-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2E)-methylbut-2-enoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl dihydrogen diphosphate]
Systematic IUPAC name O¹-{[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} O³-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2E)-methylbut-2-enoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphate
Identifiers
CAS Number	6247-62-7^Y
3D model (JSmol)	Interactive image
MeSH	tiglyl-coenzyme+A
PubChem CID	6443760
CompTox Dashboard (EPA)	DTXSID101027515
SMILES C\C=C(/C)\C(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C2N=CN=C3N)O)OP(=O)(O)O)O
Properties
Chemical formula	C₂₆H₄₂N₇O₁₇P₃S
Molar mass	849.63 g/mol
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

Tiglyl-CoA is an intermediate in the metabolism of isoleucine.^[1]^[2] It is an inhibitor of N-acetylglutamate synthetase.^[3]

References

^ ROBINSON WG; BACHHAWAT BK; COON MJ (1956). "TIGLYL COENZYME A AND a-METHYLACETOACETYL COENZYME A, INTERMEDIATES IN THE ENZYMATIC DEGRADATION OF ISOLEUCINE". Journal of Biological Chemistry. 218 (1): 391–400. doi:10.1016/S0021-9258(18)65902-2. PMID 13278346.
^ "Showing metabocard for Tiglyl-CoA (HMDB02054)". The Metabolomics Innovation Centre (TMIC).
^ Coude, F X; Sweetman, L; Nyhan, W L (1979). "Inhibition by propionyl-coenzyme A of N-acetylglutamate synthetase in rat liver mitochondria. A possible explanation for hyperammonemia in propionic and methylmalonic acidemia". Journal of Clinical Investigation. 64 (6): 1544–1551. doi:10.1172/JCI109614. PMC 371306. PMID 500823.

Amino acid metabolism metabolic intermediates

K→acetyl-CoA

lysine→	Saccharopine Allysine α-Aminoadipic acid 2-Oxoadipic acid Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA
leucine→	β-Hydroxy β-methylbutyric acid β-Hydroxy β-methylbutyryl-CoA Isovaleryl-CoA α-Ketoisocaproic acid β-Ketoisocaproic acid β-Ketoisocaproyl-CoA β-Leucine β-Methylcrotonyl-CoA β-Methylglutaconyl-CoA β-Hydroxy β-methylglutaryl-CoA
tryptophan→alanine→	N′-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

glycine→ serine→	3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde
proline→	1-Pyrroline-5-carboxylic acid
arginine→	Agmatine Ornithine Citrulline Cadaverine Putrescine
other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid
isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA
methionine→	generation of homocysteine: S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine: Cystathionine α-Ketobutyric acid + Cysteine
threonine→	α-Ketobutyric acid
propionyl-CoA→	Methylmalonyl-CoA