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Merck

A2056

Acetyl coenzyme A trisodium salt

≥93% (HPLC), powder

Synonym(s):

Acetyl-S- CoA, Acetyl CoA

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About This Item

Empirical Formula (Hill Notation):
C23H35N7O17P3S · 3Na
CAS Number:
102029-73-2
Molecular Weight:
875.52
NACRES:
NA.51
PubChem Substance ID:
24890621
UNSPSC Code:
41106305
MDL number:
MFCD00078858
Form:
powder
Assay:
≥93% (HPLC)
Solubility:
H2O: 100 mg/mL

Key Documents

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Product Name

Acetyl coenzyme A trisodium salt, ≥93% (HPLC), powder

InChI

1S/C23H38N7O17P3S.Na/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;+1/p-1/t13-,16-,17-,18?,22-;/m1./s1

SMILES string

O[C@H]1[C@](O[C@@H]([C@H]1OP(O)(O)=O)COP(OP(OCC(C)(C)[C@@H](O)C(NCCC(NCCSC(C)=O)=O)=O)(O)=O)(O)=O)([H])N2C3=NC=NC(N)=C3N=C2.[3Na]

InChI key

HNLIOWFIXSPFEC-WLYMNMRISA-M

assay

≥93% (HPLC)

form

powder

solubility

H2O: 100 mg/mL

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-CoA is an essential cofactor and carrier of acyl groups in enzymatic acetyl transfer reactions. Acetyl CoA 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 (Krebs cycle). Acetyl CoA is also a key precursor in lipid biosynthesis, and the source of all fatty acid carbons. Acetyl-CoA positively regulates the activity pyruvate carboxylase. Acetyl CoA 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.
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.
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.

Other Notes

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

Preparation Note

Prepared enzymatically

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000525914
0000525914
0000525398
0000525396
0000525396

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Virupakshi Soppina et al.
PloS one, 7(10), e48204-e48204 (2012-10-31)
The αβ-tubulin subunits of microtubules can undergo a variety of evolutionarily-conserved post-translational modifications (PTMs) that provide functional specialization to subsets of cellular microtubules. Acetylation of α-tubulin residue Lysine-40 (K40) has been correlated with increased microtubule stability, intracellular transport, and ciliary
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
Prabodh Sadana et al.
ACS chemical biology, 6(10), 1096-1106 (2011-08-06)
Thyroid hormone (T3) mediates diverse physiological functions including growth, differentiation, and energy homeostasis through the thyroid hormone receptors (TR). The TR binds DNA at specific recognition sequences in the promoter regions of their target genes known as the thyroid hormone
Whitney R Luebben et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(45), 19254-19259 (2010-10-27)
Histone posttranslational modifications and chromatin dynamics are inextricably linked to eukaryotic gene expression. Among the many modifications that have been characterized, histone tail acetylation is most strongly correlated with transcriptional activation. In Metazoa, promoters of transcriptionally active genes are generally
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