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P9716

Sigma-Aldrich

Palmitoyl coenzyme A lithium salt

≥90%

Synonym(s):

n-Hexadecanoyl Coenzyme A, Hexadecanoyl coenzyme A

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About This Item

Empirical Formula (Hill Notation):
C37H65N7O17P3S · xLi+
CAS Number:
188174-64-3
Molecular Weight:
1004.94 (free acid basis)
MDL number:
MFCD01863103
UNSPSC Code:
12352200
PubChem Substance ID:
24899057
NACRES:
NA.77

Quality Level

200

assay

≥90%

form

powder

storage temp.

−20°C

SMILES string

[Li+].CCCCCCCCCCCCCCCC(=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/C37H66N7O17P3S.Li/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44;/h24-26,30-32,36,47-48H,4-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52);/q;+1/p-1/t26-,30-,31-,32+,36-;/m1./s1

InChI key

BSAYABVAJQBKKB-NNGKVBCISA-M

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Application

Palmitoyl coenzyme A lithium salt has been used for microinjecting newt egg, to study the effect of citrate synthase inhibition in egg activation. It has also been used in reaction mix for thioesterase I (tesA) enzymatic activity assay.Palmitoyl coenzyme A lithium salt has been used in in vitro S-palmitoylation of cyclophilin D.

Biochem/physiol Actions

Palmitoyl coenzyme A (CoA) is an acyl-CoA and a precursor of 3-ketodihydrosphingosine, a key element of sphingoid base backbone during the De novo sphingolipid biosynthesis. Palmitoyl CoA is a long chain fatty acid (C16) covalently linked to Coenzyme A. Covalent attachment of palmitate is a common occurrence on a wide variety of viral and cellular proteins and plays a role in promoting membrane binding. Palmitoylation may also be a general mechanism for prolonging or potentiating G-protein signaling.
Palmitoyl coenzyme A is useful in the biosynthesis of sphingosine, a component of sphingolipids and phospholipids.β-Oxidation of Palmitoyl-CoA yields 8 acetyl-CoA molecules and 14 pairs of hydrogen atoms.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Velayoudame Parthibane et al.
The Journal of biological chemistry, 296, 100491-100491 (2021-03-05)
Serine palmitoyltransferase complex (SPT) mediates the first and rate-limiting step in the de novo sphingolipid biosynthetic pathway. The larger subunits SPTLC1 and SPTLC2/SPTLC3 together form the catalytic core while a smaller third subunit either SSSPTA or SSSPTB has been shown
Biochemistry: The Chemical Reactions of Living Cells, 992-992 (2001)
Lipid Mediators and Their Metabolism in the Brain, 245-245 (2011)
Diel light: dark cycles significantly reduce FFA accumulation in FFA producing mutants of Synechocystis sp. PCC 6803 compared to continuous light
Cheah YE, et al.
Algal research, 12, 487-496 (2015)
M D Resh
Biochimica et biophysica acta, 1451(1), 1-16 (1999-08-14)
Covalent attachment of myristate and/or palmitate occurs on a wide variety of viral and cellular proteins. This review will highlight the latest advances in our understanding of the enzymology of N-myristoylation and palmitoylation as well as the functional consequences of
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