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M4263

Sigma-Aldrich

Malonyl coenzyme A lithium salt

≥90% (HPLC)

Synonym(s):

Malonyl CoA lithium salt

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About This Item

Empirical Formula (Hill Notation):
C24H38N7O19P3S · xLi+
CAS Number:
108347-84-8
Molecular Weight:
853.58 (free acid basis)
UNSPSC Code:
41106305
PubChem Substance ID:
24896812
NACRES:
NA.51

Quality Level

200

Assay

≥90% (HPLC)

solubility

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

storage temp.

−20°C

SMILES string

[Li].CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)n2cnc3c(N)ncnc23)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O

InChI

1S/C24H38N7O19P3S.Li/c1-24(2,19(37)22(38)27-4-3-13(32)26-5-6-54-15(35)7-14(33)34)9-47-53(44,45)50-52(42,43)46-8-12-18(49-51(39,40)41)17(36)23(48-12)31-11-30-16-20(25)28-10-29-21(16)31;/h10-12,17-19,23,36-37H,3-9H2,1-2H3,(H,26,32)(H,27,38)(H,33,34)(H,42,43)(H,44,45)(H2,25,28,29)(H2,39,40,41);

InChI key

OPIJLICRFQMMJH-UHFFFAOYSA-N

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Application

Malonyl coenzyme A lithium salt has been used:
  • in Krebs Ringer bicarbonate medium for preincubation of trypsinized and re-suspended fibroblast for fatty acid oxidation assay
  • in HEPES (4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid) buffer used for scintillation proximity assay for fatty acid synthase
  • as an internal standard in the reaction mixture used for succinyl-CoA ligase assay

Biochem/physiol Actions

Coenzyme A functions as an acyl group carrier, acetyl-CoA. Malonyl Coenzyme A is a coenzyme A derivative that is utilized in fatty acid and polyketide synthesis and in the transport of α-ketoglutarate across the mitochondrial membrane. Malonyl CoA is formed by the Acetyl CoA Carboxylase-mediated carboxylation of acetyl CoA. Malonyl-CoA is exclusively used as the extender unit in the synthesis of bacterial aromatic polyketides.
Malonyl coenzyme A is a coenzyme A derivative that is utilized in fatty acid and polyketide synthesis and in the transport of α-ketoglutarate across the mitochondrial membrane. Malonyl CoA is formed by the Acetyl CoA Carboxylase-mediated carboxylation of acetyl CoA. Metabolism of glucose also yields malonyl coenzyme A. It allosterically blocks the action of carnitine palmitoyltransferase 1, which affects the transfer of long chain fatty acids into mitochondria. Inactivation of fatty acid synthase results in excess malonyl coenzyme A which leads to anorexia.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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R G Summers et al.
Biochemistry, 34(29), 9389-9402 (1995-07-25)
Streptomyces glaucescens, a Gram-positive soil bacterium, produces the polyketide antibiotic tetracenomycin (Tcm) C. To study possible biochemical connections between the biosynthesis of bacterial fatty acids and polyketides, the abundant acyl carrier protein (ACP) detected throughout the growth of the tetracenomycin
J Kalervo Hiltunen et al.
Biochimica et biophysica acta, 1797(6-7), 1195-1202 (2010-03-17)
Recent studies have revealed that mitochondria are able to synthesize fatty acids in a malonyl-CoA/acyl carrier protein (ACP)-dependent manner. This pathway resembles bacterial fatty acid synthesis (FAS) type II, which uses discrete, nuclearly encoded proteins. Experimental evidence, obtained mainly through
Characterization of fatty acid synthase activity using scintillation proximity
Weiss DR and Glickman JF
Assay and Drug Development Technologies, 1(1-2), 161-166 (2003)
Succinyl-CoA synthetase (SUCLA2) deficiency in two siblings with impaired activity of other mitochondrial oxidative enzymes in skeletal muscle without mitochondrial DNA depletion
Huang X, et al.
Molecular Genetics and Metabolism, 120(3), 213-222 (2017)
Constantina Neophytou et al.
Cell reports, 38(10), 110505-110505 (2022-03-10)
Diet is a key regulator of metabolism and interacts with the intestinal microbiome. Here, we study the role of the Drosophila intestinal stem cell (ISC)-specific biotin transporter Smvt in midgut homeostasis, infection-induced regeneration, and tumorigenesis. We show that Smvt-transported biotin
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