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
3D model (JSmol)
MeSH tiglyl-coenzyme+A
  • 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
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).
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Tiglyl-CoA is an intermediate in the metabolism of isoleucine.[1][2] It is an inhibitor of N-acetylglutamate synthetase.[3]

References

  1. ^ 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.
  2. ^ "Showing metabocard for Tiglyl-CoA (HMDB02054)". The Metabolomics Innovation Centre (TMIC).
  3. ^ 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.


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