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Merck

A2181

Acetyl coenzyme A lithium salt

≥93% (HPLC)

Sinónimos:

Acetyl-CoA, Acetyl-S-CoA Li3

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Fórmula empírica (notación de Hill):
C23H38N7O17P3S · xLi+
Número CAS:
32140-51-5
Peso molecular:
809.57 (free acid basis)
NACRES:
NA.51
PubChem Substance ID:
24890633
UNSPSC Code:
41106305
MDL number:
MFCD00167406

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Nombre del producto

Acetyl coenzyme A lithium salt, ≥93% (HPLC)

InChI

1S/C23H38N7O17P3S.3Li/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30;;;/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38);;;/q;3*+1/p-3/t13-,16-,17-,18+,22-;;;/m1.../s1

SMILES string

[Li+].[Li+].[Li+].CC(=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 key

FTRFBNATWBKIQU-JHJDYNLLSA-K

assay

≥93% (HPLC)

form

powder

solubility

H2O: soluble 100 mg/mL, clear, colorless

storage temp.

−20°C

Quality Level

300

Gene Information

human ... CHAT(1103), HAT1(8520), KAT2A(2648), KAT2B(8850), KAT5(10524)
mouse ... HAT1(107435), KAT2A(14534), KAT2B(18519), KAT5(81601)
rat ... HAT1(296501), KAT2A(303539), KAT2B(301164), KAT5(192218)

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Application

Acetyl coenzyme A is suitable in CAT reporter assay for the measurement of chloramphenicol acetyltransferase by incubating the cell extract with 0.1 μCi [14C] chloramphenicol and 0.5mM acetyl-CoA.
An essential cofactor in enzymatic acetyl transfer reactions.

Biochem/physiol Actions

Acetyl-CoA is an essential cofactor and carrier of acyl groups in enzymatic acetyl transfer reactions. It is formed either by the oxidative decarboxylation of pyruvate in mitochondria, by the oxidation of long-chain fatty acids, or by the oxidative degradation of certain amino acids. Acetyl-CoA is the starting compound for the citric acid cycle (Kreb′s cycle). It is also a key precursor in lipid biosynthesis, and the source of all fatty acid carbons. Acetyl-CoA positively regulates the activity pyruvate carboxylase. It is a precursor of the neurotransmitter acetylcholine. Histone acetylases (HAT) use Acetyl-CoA as the donor for the acetyl group use in the post-translational acetylation reactions of histone and non-histone proteins.
Alterations in the gene encoding acetyl-CoA have been linked to Alzheimer′s disease and mild cognitive impairment. Defects in the gene cause myasthenic syndrome associated with episodic apnea.

General description

This moisture-sensitive powder should be stored desiccated at −20°C.

Other Notes

For more more technical information and a complete list of Coenzyme A deriviatives visit the Acyl Transfer Reagents Resource.

Preparation Note

Acetyl CoA is soluble in deionized water at 100 mg/mL. Acetyl CoA is stable in neutral and moderately acidic solutions but will hydrolyze in alkaline and strongly acidic solutions. Aqueous solutions stored in single-use aliquots are stable for up to two weeks at −20°C and up to 6 months at −80°C.
Prepared enzymatically

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
0000499688
0000499688
0000499678
0000499678
0000472895

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Devis Sinani et al.
Journal of virology, 85(23), 12124-12133 (2011-09-23)
Bovine herpesvirus 1 (BHV-1) infection induces clinical symptoms in the upper respiratory tract, inhibits immune responses, and can result in life-threatening secondary bacterial infections. Following acute infection, BHV-1 establishes latency in sensory neurons within trigeminal ganglia. Periodically, reactivation from latency
Prabhjot Singh et al.
Protein and peptide letters, 18(5), 507-517 (2011-01-18)
The distinct biochemical function of endoplasmic reticulum (ER) protein Calreticulin (CR) catalyzing the transfer of acyl group from acyloxycoumarin to a receptor protein was termed calreticulin transacylase (CRTAase). The present study, unlike the previous reports of others utilizing CR-deficient cells
Juliette Adjo Aka et al.
Handbook of experimental pharmacology, 206, 1-12 (2011-09-01)
Lysine (K) acetylation refers to transfer of the acetyl moiety from acetyl-CoA to the ε-amino group of a lysine residue. This is posttranslational and reversible, with its level dynamically maintained by lysine acetyltransferases (KATs) and deacetylases (KDACs). Traditionally, eukaryotic KDACs
Simone Kraner et al.
Archives of neurology, 60(5), 761-763 (2003-05-21)
The syndrome of congenital myasthenia with episodic apnea (CMS-EA) was previously found to be due to mutations in the choline acetyltransferase gene (CHAT). To identify the mutations underlying CMS-EA in a Turkish multiplex family. Direct sequencing of the CHAT gene.
Dennis Shin-Shian Hsu et al.
Cancer cell, 26(4), 534-548 (2014-10-15)
Snail is primarily known as a transcriptional repressor that induces epithelial-mesenchymal transition by suppressing adherent proteins. Emerging evidence suggests that Snail can act as an activator; however, the mechanism and biological significance are unclear. Here, we found that CREB-binding protein
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