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M1762

Sigma-Aldrich

Methylmalonyl coenzyme A tetralithium salt hydrate

≥90% (HPLC)

Synonym(s):

α-Methylmalonyl coenzyme A tetralithium salt, MM-CoA

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About This Item

Empirical Formula (Hill Notation):
C25H36Li4N7O19P3S · xH2O
CAS Number:
104809-02-1
Molecular Weight:
891.34 (anhydrous basis)
MDL number:
MFCD10567443
UNSPSC Code:
41106305
PubChem Substance ID:
24896685

Quality Level

200

Assay

≥90% (HPLC)

storage temp.

−20°C

SMILES string

[Li+].[Li+].[Li+].[Li+].O.CC(C([O-])=O)C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(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

InChI

1S/C25H40N7O19P3S.4Li.H2O/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);;;;;1H2/q;4*+1;/p-4/t12?,13-,16-,17-,18+,22-;;;;;/m1...../s1

InChI key

ANDKBBZIPFWODN-WLVKLPLXSA-J

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Application

Coenzyme A functions as an acyl group carrier, acetyl-CoA. Methylmalonyl coenzyme A (MM-CoA) is a substrate used to study the specificity and kinetics of enzymes such as methylmalonyl Coenzyme A mutase (succinyl-Ca forming), methylmalonyl-CoA decarboxylase (EC 4.1.1.41), and methylmalonyl-CoA hydrolase (EC 3.1.2.17).
Methylmalonyl coenzyme A (CoA) has been used in the preparation of the calibration curve in ultra-performance liquid chromatography-mass spectrometry (UPLC-MS/MS). It has also been used in the measurement of methylmalonyl-CoA mutase and methylmalonyl-CoA epimerase activity.

Biochem/physiol Actions

Methylmalonyl coenzyme A (CoA) is a catabolite of odd-chain fatty acids, cholesterol and few amino acids like valine, isoleucine, methionine, threonine. It is produced by the activity of the enzyme propionyl-CoA carboxylase(PCC). Methylmalonyl coenzyme A (CoA) is converted to succinyl-CoA by the methylmalonyl-CoA mutase (MCM) and vitamin B12 as the cofactor. Either a low MCM activity or an altered metabolism of vitamin B12 causes the inherited metabolic disease methylmalonic acidemia (MMA).

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Valentin Cracan et al.
The Journal of biological chemistry, 285(1), 655-666 (2009-10-30)
Coenzyme B(12) is used by two highly similar radical enzymes, which catalyze carbon skeleton rearrangements, methylmalonyl-CoA mutase and isobutyryl-CoA mutase (ICM). ICM catalyzes the reversible interconversion of isobutyryl-CoA and n-butyryl-CoA and exists as a heterotetramer. In this study, we have
Determination of methylmalonyl coenzyme A by ultra high-performance liquid chromatography tandem mass spectrometry for measuring propionyl coenzyme A carboxylase activity in patients with propionic acidemia
Gotoh K, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 1046, 195-199 (2017)
Dominique Padovani et al.
Nature chemical biology, 4(3), 194-196 (2008-02-12)
The reactivity and relative rarity of most cofactors pose challenges for their delivery to target enzymes. Using kinetic analyses, we demonstrate that adenosyltransferase, which catalyzes the final step in the assimilation of coenzyme B12, directly transfers the cofactor to methylmalonyl
Filippo Carlucci et al.
Electrophoresis, 28(12), 1921-1925 (2007-05-23)
Methylmalonyl-coenzyme A mutase (MCM) is a 5'-deoxyadenosylcobalamin-linked mitochondrial enzyme that catalyzes the isomerization of L-methylmalonyl-coenzyme A to succinyl-coenzyme A. We described a method for methylmalonyl-CoA and succinyl-CoA separation by CE, suitable for the evaluation of MCM activity. The working conditions
Assay for methylmalonyl coenzyme A mutase activity based on determination of succinyl coenzyme A by ultrahigh-performance liquid chromatography tandem mass spectrometry
Gotoh K, et al.
Analytical and Bioanalytical Chemistry, 407(18), 5281-5286 (2015)
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