Succinyl-CoA

Succinyl-CoA

Identifiers
CAS Number	604-98-8
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15380
ChemSpider	83179
ECHA InfoCard	100.009.163
MeSH	succinyl-coenzyme+A
PubChem CID	92133
CompTox Dashboard (EPA)	DTXSID40975809
InChI 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)/t13-,18-,19-,20+,24-/m1/s1 Key: VNOYUJKHFWYWIR-ITIYDSSPSA-N InChI=1/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)/t13-,18-,19-,20+,24-/m1/s1 Key: VNOYUJKHFWYWIR-ITIYDSSPBJ
SMILES O=C(O)CCC(=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	C25H40N7O19P3S
Molar mass	867.608
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Succinyl-coenzyme A, abbreviated as succinyl-CoA (/ˌsʌksɪnəlˌkoʊˈeɪ/) or SucCoA, is a thioester of succinic acid and coenzyme A.

Sources

It is an important intermediate in the citric acid cycle, where it is synthesized from α-ketoglutarate by α-ketoglutarate dehydrogenase through decarboxylation. During the process, coenzyme A is added.

With B12 as an enzymatic cofactor, it is also synthesized from propionyl CoA, the odd-numbered fatty acid, which cannot undergo beta-oxidation.^[1] Propionyl-CoA is carboxylated to D-methylmalonyl-CoA, isomerized to L-methylmalonyl-CoA, and rearranged to yield succinyl-CoA via a vitamin B₁₂-dependent enzyme. Succinyl-CoA is an intermediate of the citric acid cycle and can be readily incorporated there.

Fate

It is converted into succinate through the hydrolytic release of coenzyme A by succinyl-CoA synthetase (succinate thiokinase).

Another fate of succinyl-CoA is porphyrin synthesis, where succinyl-CoA and glycine are combined by ALA synthase to form δ-aminolevulinic acid (dALA). This process is the committed step in the biosynthesis of porfobilinogen and thus hemoglobin.

Formation

Succinyl CoA can be formed from methylmalonyl CoA through the utilization of deoxyadenosyl-B₁₂ (deoxyadenosylcobalamin) by the enzyme methylmalonyl-CoA mutase. This reaction, which requires vitamin B₁₂ as a cofactor, is important in the catabolism of some branched-chain amino acids as well as odd-chain fatty acids.

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles. ^{[§ 1]}

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|{{{bSize}}}px|alt=TCACycle_WP78 edit]]

TCACycle_WP78 edit

1. ^ The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78".

References

Citric acid cycle metabolic pathway
Acetyl-CoA + H 2O	Oxaloacetate NADH +H+ NAD+ Malate H2O Fumarate FADH2 FAD Succinate CoA + ATP (GTP) Pi + ADP (GDP) Succinyl-CoA
			NADH + H+ + CO 2
CoA			NAD+
	Citrate H 2O cis-Aconitate H 2O Isocitrate NAD(P)+ NAD(P)H + H+ Oxalosuccinate CO 2 2-oxoglutarate