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S1129

Sigma-Aldrich

Succinyl coenzyme A sodium salt

≥85%

Synonym(s):

Succinyl CoA sodium salt

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About This Item

Empirical Formula (Hill Notation):
C25H40N7O19P3S
CAS Number:
108347-97-3
Molecular Weight:
867.61
UNSPSC Code:
41106305
PubChem Substance ID:
24899460
NACRES:
NA.51

Assay

≥85%

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

[Na+].[Na+].CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)([O-])=O)n2cnc3c(N)ncnc23)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC([O-])=O

InChI

1S/C25H40N7O19P3S/c1-25(2,20(38)23(39)28-6-5-14(33)27-7-8-55-16(36)4-3-15(34)35)10-48-54(45,46)51-53(43,44)47-9-13-19(50-52(40,41)42)18(37)24(49-13)32-12-31-17-21(26)29-11-30-22(17)32/h11-13,18-20,24,37-38H,3-10H2,1-2H3,(H,27,33)(H,28,39)(H,34,35)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/p-2/t13-,18-,19-,20?,24-/m1/s1

InChI key

VNOYUJKHFWYWIR-FZEDXVDRSA-L

Application

Succinyl coenzyme A sodium salt has been used:
  • for the nonenzymatic succinylation of lysine in vitro,
  • as a substrate for adipic acid biosynthesis in recombinant E. coli
  • in isocitrate dehydrogenase (ICDH) treatment for the succinylation of proteins
  • as a substrate to study the specificity and kinetics of enzymes such as acetate:succinate CoA-transferase and 5-aminolevulinate synthase (ALA synthase)

Biochem/physiol Actions

Succinyl CoA is an intermediate in the citric acid cycle. It is formed by α-ketoglutarate dehydrogenase by the decarboxylation of α-ketoglutarate. Succinyl CoA is also formed from propionyl CoA during the β-oxidation of odd-chain fatty acids. Succinyl CoA serves as a precursor in heme synthesis. It is also required for the oxidation of ketone bodies.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Jeong-Ah Shin et al.
Journal of microbiology and biotechnology, 17(9), 1579-1584 (2007-12-08)
5-aminolevulinate (ALA) synthase (E.C. 2.3.1.37), which mediates the pyridoxal phosphate-dependent condensation of glycine and succinyl-CoA, encoded by the Rhodobacter sphaeroides hemA gene, enables Escherichia coli strains to produce ALA at a low level. To study the effect of the enhanced
Marc Schürmann et al.
Acta crystallographica. Section D, Biological crystallography, 71(Pt 6), 1360-1372 (2015-06-10)
3-Sulfinopropionyl-coenzyme A (3SP-CoA) desulfinase (AcdDPN7; EC 3.13.1.4) was identified during investigation of the 3,3'-dithiodipropionic acid (DTDP) catabolic pathway in the betaproteobacterium Advenella mimigardefordensis strain DPN7(T). DTDP is an organic disulfide and a precursor for the synthesis of polythioesters (PTEs) in
Koen W A van Grinsven et al.
The Journal of biological chemistry, 283(3), 1411-1418 (2007-11-21)
Acetate:succinate CoA-transferases (ASCT) are acetate-producing enzymes in hydrogenosomes, anaerobically functioning mitochondria and in the aerobically functioning mitochondria of trypanosomatids. Although acetate is produced in the hydrogenosomes of a number of anaerobic microbial eukaryotes such as Trichomonas vaginalis, no acetate producing
Koen W A van Grinsven et al.
Molecular and biochemical parasitology, 164(1), 74-79 (2008-12-24)
Fasciola hepatica contains anaerobically functioning mitochondria that produce acetate and propionate, the main endproducts excreted by this parasite. The final reactions in the pathways leading to these endproducts are performed by acetate:succinate CoA-transferase (ASCT) and propionate:succinate CoA-transferase (PSCT), respectively. The
Generation of succinyl-coenzyme A in photosynthetic bacteria
Beatty J T and Gest H
Archives of Microbiology, 129, 335-340 (1981)
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