Glutaconyl-CoA

Glutaconyl-CoA
Names
IUPAC name
(3E)-5-[(2-{3-[(2R)-4-{[1,3-Dihydroxy-1,3-dioxo-3-(3′-O-phosphonoadenosin-5′-O-yl)-1λ5,3λ5-diphosphoxan-1-yl]oxy}-3,3-dimethylbutanamido]propanamido}ethyl)sulfanyl]-5-oxopent-3-enoic acid
Systematic IUPAC name
(9R,20E)-1-[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]-3,5,9-trihydroxy-8,8-dimethyl-3,5,10,14,19-pentaoxo-2,4,6-trioxa-18-thia-11,15-diaza-3λ5,5λ5-diphosphatricos-20-en-23-oic acid
Other names
Glutaconyl-coenzyme A
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
MeSH glutaconyl-coenzyme+A
PubChem CID
UNII
InChI
  • InChI=1S/C26H40N7O19P3S/c1-26(2,21(39)24(40)29-7-6-15(34)28-8-9-56-17(37)5-3-4-16(35)36)11-49-55(46,47)52-54(44,45)48-10-14-20(51-53(41,42)43)19(38)25(50-14)33-13-32-18-22(27)30-12-31-23(18)33/h3,5,12-14,19-21,25,38-39H,4,6-11H2,1-2H3,(H,28,34)(H,29,40)(H,35,36)(H,44,45)(H,46,47)(H2,27,30,31)(H2,41,42,43)/b5-3+/t14-,19-,20-,21+,25-/m1/s1 ☒N
    Key: URTLOTISFJPPOU-DEGQQWIJSA-N ☒N
  • InChI=1/C26H40N7O19P3S/c1-26(2,21(39)24(40)29-7-6-15(34)28-8-9-56-17(37)5-3-4-16(35)36)11-49-55(46,47)52-54(44,45)48-10-14-20(51-53(41,42)43)19(38)25(50-14)33-13-32-18-22(27)30-12-31-23(18)33/h3,5,12-14,19-21,25,38-39H,4,6-11H2,1-2H3,(H,28,34)(H,29,40)(H,35,36)(H,44,45)(H,46,47)(H2,27,30,31)(H2,41,42,43)/b5-3+/t14-,19-,20-,21+,25-/m1/s1
    Key: URTLOTISFJPPOU-DEGQQWIJBS
SMILES
  • O=C(O)C/C=C/C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3OP(=O)(O)O
Properties
Chemical formula
 C26H40N7O19P3S
Molar mass 879.62 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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Infobox references

Glutaconyl-CoA is an intermediate in the metabolism of lysine.[1] It is an organic compound containing a coenzyme substructure, which classifies it as a fatty ester lipid molecule. Being a lipid makes the molecule hydrophobic, which makes it insoluble in water. The molecule has a molecular formula of C26H40N7O19P3S, and a molecular weight 879.62 grams per mole.[2]

Glutaconyl-CoA is postulated to be the main toxin in glutaric aciduria type 1.[3] In certain fermentative bacteria, glutaconyl-CoA decarboxylation is catalyzed by a Na+-dependent decarboxylase (EC 7.2.4.5) and is coupled with Na+ ion translocation, which creates a sodium-motive force as an alternate energy source for these organisms.[4]

See also

  • Glutaconate CoA-transferase
  • Glutaconyl-CoA decarboxylase

References

  1. ^ Trefely, Sophie; Lovell, Claudia D.; Snyder, Nathaniel W.; Wellen, Kathryn E. (2020). "Compartmentalised acyl-CoA metabolism and roles in chromatin regulation". Molecular Metabolism. 38 100941. doi:10.1016/j.molmet.2020.01.005. PMC 7300382. PMID 32199817. Glutaryl-CoA is a product of tryptophan and lysine catabolism preceding crotonoyl-CoA production in the mitochondria
  2. ^ "Human Metabolome Database: Showing metabocard for Glutaconyl-CoA (HMDB0001290)". hmdb.ca. Retrieved 2022-10-18.
  3. ^ Lehnert, Willy; Sass, Jörn Oliver (January 2005). "Glutaconyl-CoA is the main toxic agent in glutaryl-CoA dehydrogenase deficiency (glutaric aciduria type I)". Medical Hypotheses. 65 (2): 330–333. doi:10.1016/j.mehy.2005.02.021. PMID 15922108.
  4. ^ Kress, Daniel; Brügel, Daniela; Schall, Iris; Linder, Dietmar; Buckel, Wolfgang; Essen, Lars-Oliver (October 2009). "An Asymmetric Model for Na+-translocating Glutaconyl-CoA Decarboxylases". Journal of Biological Chemistry. 284 (41): 28401–28409. doi:10.1074/jbc.m109.037762. PMC 2788889. PMID 19654317.


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