Methylmalonyl-CoA

Methylmalonyl-CoA is the thioester consisting of coenzyme A linked to methylmalonic acid. It is an important intermediate in the biosynthesis of many organic compounds as well as in the process of carbon assimilation.[1]

Methylmalonyl-CoA

Names
IUPAC name (9R)-1-[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydro-2-furanyl]-3,5,9-trihydroxy-8,8,20-trimethyl-10,14,19-trioxo-2,4,6-trioxa-18-thia-11,15-diaza-3,5-diphosphahenicosan-21-oic acid 3,5-dioxide (non-preferred name)
Identifiers
CAS Number	1264-45-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16625
ChemSpider	110440
IUPHAR/BPS	5223
PubChem CID	123909
CompTox Dashboard (EPA)	DTXSID20925529
InChI InChI=1S/C25H40N7O19P3S/c1-12(23(37)38)24(39)55-7-6-27-14(33)4-5-28-21(36)18(35)25(2,3)9-48-54(45,46)51-53(43,44)47-8-13-17(50-52(40,41)42)16(34)22(49-13)32-11-31-15-19(26)29-10-30-20(15)32/h10-13,16-18,22,34-35H,4-9H2,1-3H3,(H,27,33)(H,28,36)(H,37,38)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t12?,13-,16-,17-,18+,22-/m1/s1 Key: MZFOKIKEPGUZEN-FBMOWMAESA-N InChI=1/C25H40N7O19P3S/c1-12(23(37)38)24(39)55-7-6-27-14(33)4-5-28-21(36)18(35)25(2,3)9-48-54(45,46)51-53(43,44)47-8-13-17(50-52(40,41)42)16(34)22(49-13)32-11-31-15-19(26)29-10-30-20(15)32/h10-13,16-18,22,34-35H,4-9H2,1-3H3,(H,27,33)(H,28,36)(H,37,38)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t12?,13-,16-,17-,18+,22-/m1/s1 Key: MZFOKIKEPGUZEN-FBMOWMAEBZ
SMILES CC(C(=O)O)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=C(N=CN=C32)N)O)OP(=O)(O)O)O
Properties
Chemical formula	C25H40N7O19P3S
Molar mass	867.608 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

Biosynthesis and conversions

Methylmalonyl-CoA is formed from propionyl-CoA by propionyl-CoA carboxylase by help of biotin (vitamin B₇). It is converted into succinyl-CoA by methylmalonyl-CoA mutase, in a reaction that requires vitamin B₁₂ as a cofactor. In this way, it enters the Krebs cycle. The following diagram demonstrates the aforementioned reactions:[2]

Propionyl CoA → Methylmalonyl CoA → Succinyl CoA

See also

• Methylmalonyl CoA epimerase

References

1. Tabita, F. R., "The hydroxypropionate pathway of CO₂ fixation: Fait accompli", Proceedings of the National Academy of Sciences 2009, vol. 106, 21015-21016. doi:10.1073/pnas.0912486107
2. Nelson, David L.; Cox, Michael M. (2005). Principles of Biochemistry (4th ed.). New York: W. H. Freeman. ISBN 0-7167-4339-6.