Succinyl-CoA

Succinyl-CoA
Identifiers

CAS Number	604-98-8^N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:15380^Y
ChemSpider	83179^Y
ECHA InfoCard	100.009.163
MeSH	succinyl-coenzyme+A
PubChem	92133
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^Y Key: VNOYUJKHFWYWIR-ITIYDSSPSA-N^Y 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).
N verify (what is ^YN ?)
Infobox references

Succinyl-Coenzyme A, abbreviated as Succinyl-CoA (/ˌsʌksᵻnəlˌkoʊˈeɪ/) or SucCoA, is a combination 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).

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=TCA Cycle edit]]

TCA Cycle edit

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

References

↑ Halarnkar PP, Blomquist GJ (1989). "Comparative aspects of propionate metabolism". Comp. Biochem. Physiol., B. 92 (2): 227–31. doi:10.1016/0305-0491(89)90270-8. PMID 2647392.

Citric acid cycle metabolic pathway
			Oxaloacetate			Malate			Fumarate			Succinate			Succinyl-CoA


Acetyl-CoA				NADH + H⁺	NAD⁺			H₂O		FADH₂	FAD		CoA + ATP(GTP)	P_i + ADP(GDP)
	+	H₂O														NADH + H⁺ + CO₂
		CoA														NAD⁺
					H₂O		H₂O			NAD(P)⁺	NAD(P)H + H⁺			CO₂


			Citrate			cis-Aconitate			Isocitrate			Oxalosuccinate			α-Ketoglutarate

Amino acid metabolism metabolic intermediates

K→acetyl-CoA

lysine→	Saccharopine Allysine α-Aminoadipic acid α-Ketoadipate Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA

leucine→	α-Ketoisocaproic acid β-hydroxy β-methylbutyric acid β-hydroxy β-methylbutyryl-CoA Isovaleryl-CoA 3-Methylcrotonyl-CoA 3-Methylglutaconyl-CoA HMG-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

G→pyruvate→citrate

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

G→glutamate→
α-ketoglutarate

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

G→propionyl-CoA→
succinyl-CoA

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 alpha-Ketobutyric acid+Cysteine

threonine→	α-Ketobutyric acid

propionyl-CoA→	Methylmalonyl-CoA

G→fumarate

phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid Homogentisic acid 4-Maleylacetoacetic acid

G→oxaloacetate

see urea cycle

Other

Cysteine metabolism	Cysteine sulfinic acid

This article is issued from Wikipedia - version of the 5/24/2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.