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Merck

M1762

Sigma-Aldrich

甲基丙二酰辅酶A 四锂盐 水合物

≥90% (HPLC)

别名:

α-甲基丙二酰辅酶 A 四锂盐, 甲基丙二酰辅酶A

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1 MG
$208.00
5 MG
$966.00
25 MG
$2,800.00

About This Item

经验公式(希尔记法):
C25H36Li4N7O19P3S · xH2O
分子量:
891.34 (anhydrous basis)
MDL编号:
UNSPSC代码:
41106305
PubChem化学物质编号:
NACRES:
NA.51

$208.00


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方案

≥90% (HPLC)

表单

powder

溶解性

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

储存温度

−20°C

SMILES字符串

[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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应用

甲基丙二酰辅酶 A (CoA) 已用于超高效液相色谱-质谱法 (UPLC-MS/MS) 中校准曲线的制备。[1][2] 也用于测定甲基丙二酰辅酶 a 变位酶和甲基丙二酰辅酶 a 差向异构酶活性。[3]
辅酶 A 作为酰基载体,即乙酰辅酶 A 发挥作用。甲基丙二酰辅酶 A (MM-CoA) 是用于研究甲基丙二酰辅酶 A 变位酶(琥珀酰-Ca 形成)、甲基丙二酰辅酶 A 脱羧酶 (EC 4.1.1.41) 和甲基丙二酰辅酶 A 水解酶 (EC 3.1.2.17) 等酶的特异性和动力学的底物。

生化/生理作用

甲基丙二酰辅酶 A (CoA) 是单链脂肪酸、胆固醇和少量氨基酸(如缬氨酸、异亮氨酸、蛋氨酸、苏氨酸)的降解产物。[1][2] 由丙酰辅酶 a 羧化酶 (PCC) 的活性产生。[2]甲基丙二酰辅酶 A (CoA) 通过甲基丙二酰辅酶 A 变位酶 (MCM) 和维生素 B12 作为辅助因子转化为琥珀酰辅酶 A。低 MCM 活性或维生素 B12 代谢改变导致遗传代谢病甲基丙二酸血症 (MMA)。[1]

象形图

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警示用语:

Warning

危险声明

危险分类

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

靶器官

Respiratory system

储存分类代码

11 - Combustible Solids

WGK

WGK 3

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves


历史批次信息供参考:

分析证书(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
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.
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)
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)
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

Questions

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

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

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