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A5837

Sigma-Aldrich

Arachidonoyl coenzyme A lithium salt

≥85%

Synonym(s):

Arachidonoyl CoA lithium salt, cis,cis,cis,cis-5,8,11,14-Eicosatetraenoyl coenzyme A lithium salt

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About This Item

Empirical Formula (Hill Notation):
C41H66N7O17P3S · xLi+
CAS Number:
188174-63-2
Molecular Weight:
1053.99 (free acid basis)
MDL number:
MFCD01311885
UNSPSC Code:
41106305
PubChem Substance ID:
24891026
NACRES:
NA.51

Quality Level

200

Assay

≥85%

form

powder

storage temp.

−20°C

SMILES string

[Li+].CCCCC\C=C\C\C=C\C\C=C\C\C=C\CCCC(=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/C41H66N7O17P3S.Li/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-32(50)69-25-24-43-31(49)22-23-44-39(53)36(52)41(2,3)27-62-68(59,60)65-67(57,58)61-26-30-35(64-66(54,55)56)34(51)40(63-30)48-29-47-33-37(42)45-28-46-38(33)48;/h8-9,11-12,14-15,17-18,28-30,34-36,40,51-52H,4-7,10,13,16,19-27H2,1-3H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56);/q;+1/p-1/b9-8+,12-11+,15-14+,18-17+;/t30-,34-,35-,36+,40-;/m1./s1

InChI key

PFJKRDANWCBXHE-VKSULDSYSA-M

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Application

Arachidonoyl coenzyme (Arachidonoyl CoA) is used as a substrate for the long-chain N-acylation of glycines by enzymes such as glycine N-acyltransferase-like 2 (GLYATL2) and of acytransferases such as lysophosphatidic acid acyltransferase (CGI-58/ABHD5). Arachidonoyl CoA is used as a charged membrane-impermeant analog of arachidonic acid (AA). Arachidonoyl CoA is used in the synthesis of arachidonoyl amino acids by cytochrome c.
Arachidonoyl coenzyme A lithium salt may be used as a substrate for lysophosphatidylcholine acyltransferase 3 (LPCAT3).

Biochem/physiol Actions

Arachidonoyl CoA is used as a charged membrane-impermeable analog of arachidonic acid (AA). It is used as a substrate for the long-chain N-acylation of glycines by enzymes such as glycine N-acyltransferase-like 2 (GLYATL2) in the presence of cytochrome c.

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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A novel assay for measuring recombinant human lysophosphatidylcholine acyltransferase 3 activity
Du X, et al.
FEBS Open Bio, 9(10), 1734-1743 (2019)
The emerging role of acyl-CoA thioesterases and acyltransferases in regulating peroxisomal lipid metabolism
Hunt MC, et al.
Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease, 1822(9), 1397-1410 (2012)
Valerie Yeung-Yam-Wah et al.
Cell calcium, 47(1), 77-83 (2009-12-19)
Arachidonic acid (AA) is generated in the pancreatic islets during glucose stimulation. We investigated whether AA activated extracellular Ca(2+) entry in rat pancreatic beta cells via a pathway that was independent of the activation of voltage-gated Ca(2+) channels. The AA
Jeffrey M McCue et al.
Prostaglandins & other lipid mediators, 90(1-2), 42-48 (2009-08-18)
Arachidonoyl amino acids are a class of endogenous lipid messengers that are expressed in the mammalian central nervous system and peripherally. While several of their prominent pharmacologic effects have been documented, the mechanism by which arachidonoyl amino acids are biosynthesized
Effects of fatty acids on BK channels in GH3cells
Denson D, et al.
American Journal of Physiology. Cell Physiology, 279(4), C1211-C1219 (2000)
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