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Merck

M1762

Sigma-Aldrich

Methylmalonyl coenzyme A tetralithium salt hydrate

≥90% (HPLC)

Sinónimos:

α-Methylmalonyl coenzyme A tetralithium salt, MM-CoA

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1 MG
MXP 2,942.00
5 MG
MXP 12,261.00
25 MG
MXP 39,655.00

MXP 2,942.00


Fecha estimada de envío17 de abril de 2025



Seleccione un Tamaño

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1 MG
MXP 2,942.00
5 MG
MXP 12,261.00
25 MG
MXP 39,655.00

About This Item

Fórmula empírica (notación de Hill):
C25H36Li4N7O19P3S · xH2O
Número de CAS:
Peso molecular:
891.34 (anhydrous basis)
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

MXP 2,942.00


Fecha estimada de envío17 de abril de 2025


Quality Level

assay

≥90% (HPLC)

form

powder

solubility

H2O: soluble-50 mg/mL, clear, colorless

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).[1][2] It has also been used in the measurement of methylmalonyl-CoA mutase and methylmalonyl-CoA epimerase activity.[3]

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.[1][2] It is produced by the activity of the enzyme propionyl-CoA carboxylase(PCC).[2] 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).[1]

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Epimerase (Msed_0639) and mutase (Msed_0638 and Msed_2055) convert (S)-methylmalonyl-coenzyme A (CoA) to succinyl-CoA in the Metallosphaera sedula 3-hydroxypropionate/4-hydroxybutyrate cycle
Han Y, et al.
Applied and Environmental Microbiology, 78(17), 6194-6202 (2012)
Csaba Paizs et al.
Bioorganic chemistry, 36(6), 261-264 (2008-08-01)
The reported presence of a coenzyme B12-dependent methylmalonyl-CoA mutase in potatoes has been reexamined. The enzyme converting methylmalonyl-CoA was purified to electrophoretic homogeneity. Examination of the reaction product by 1H, 31P NMR and mass spectrometry revealed that it was methylmalonyl-3'-dephospho-CoA.
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)
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
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)

Questions

  1. Is this (S)-methylmalonyl-CoA?

    1 answer
    1. This product is a mixture of R and S stereoisomers.

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