900400 | Palmitic acid (15-yne)

15-hexadecynoic acid


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Palmitic acid (15-yne)

Palmitic acid (15-yne)

15-hexadecynoic acid

Alkynyl palmitic acid (aPA) is a modified palmitic acid with an ω-terminal alkyne. The terminal alkyne group can be used in a highly specific linking reaction with azide-containing reagents, known as ‘click chemistry’. The use of aPA in isolating palmitoylated proteins has been described (see References).

Hygroscopic
No
Light Sensitive
No
Molecular Formula
C16H28O2
Percent Composition
C 76.14%, H 11.18%, O 12.68%
Purity
>99%
Stability
1 Years
Storage Temperature
-20°C
CAS Number
99208-90-9
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
252.392
Exact Mass
252.209
Synonyms
aPA

Ticho AL, Malhotra P, Manzella CR, Dudeja PK, Saksena S, Gill RK, Alrefai WA. S-Acylation modulates the function of the apical sodium-dependent bile acid transporter in human cells. J Biol Chem. 2020 Feb 18:jbc.RA119.011032. doi: 10.1074/jbc.RA119.011032. Epub ahead of print. PMID: 32071081.

PubMed ID: 32071081

Tallman KA, Armstrong MD, Milne SB, Marnett LJ, Brown HA, Porter NA. Cobalt carbonyl complexes as probes for alkyne-tagged lipids. J Lipid Res. 2013 Mar;54(3):859-68. doi: 10.1194/jlr.D033332. Epub 2013 Jan 10. PMID: 23307946; PMCID: PMC3617960.

PubMed ID: 23307946

Milne SB, Tallman KA, Serwa R, Rouzer CA, Armstrong MD, Marnett LJ, Lukehart CM, Porter NA, Brown HA. Capture and release of alkyne-derivatized glycerophospholipids using cobalt chemistry. Nat Chem Biol. 2010 Mar;6(3):205-207. doi: 10.1038/nchembio.311. Epub 2010 Jan 24. PMID: 20098428; PMCID: PMC2822082.

PubMed ID: 20098428

Jiang H, Khan S, Wang Y, Charron G, He B, Sebastian C, Du J, Kim R, Ge E, Mostoslavsky R, Hang HC, Hao Q, Lin H. SIRT6 regulates TNF-α secretion through hydrolysis of long-chain fatty acyl lysine. Nature. 2013 Apr 4;496(7443):110-3. doi: 10.1038/nature12038. PMID: 23552949; PMCID: PMC3635073.

PubMed ID: 23552949

Thiele C, Papan C, Hoelper D, Kusserow K, Gaebler A, Schoene M, Piotrowitz K, Lohmann D, Spandl J, Stevanovic A, Shevchenko A, Kuerschner L. Tracing fatty acid metabolism by click chemistry. ACS Chem Biol. 2012 Dec 21;7(12):2004-11. doi: 10.1021/cb300414v. Epub 2012 Oct 2. PMID: 22999348.

PubMed ID: 22999348

Gao X, Arenas-Ramirez N, Scales SJ, Hannoush RN. Membrane targeting of palmitoylated Wnt and Hedgehog revealed by chemical probes. FEBS Lett. 2011 Aug 4;585(15):2501-6. doi: 10.1016/j.febslet.2011.06.033. Epub 2011 Jul 2. PMID: 21740904.

PubMed ID: 21740904

Yap MC, Kostiuk MA, Martin DD, Perinpanayagam MA, Hak PG, Siddam A, Majjigapu JR, Rajaiah G, Keller BO, Prescher JA, Wu P, Bertozzi CR, Falck JR, Berthiaume LG. Rapid and selective detection of fatty acylated proteins using omega-alkynyl-fatty acids and click chemistry. J Lipid Res. 2010 Jun;51(6):1566-80. doi: 10.1194/jlr.D002790. Epub 2009 Dec 21. PMID: 20028662; PMCID: PMC3035521.

PubMed ID: 20028662

Martin BR, Cravatt BF. Large-scale profiling of protein palmitoylation in mammalian cells. Nat Methods. 2009 Feb;6(2):135-8. doi: 10.1038/nmeth.1293. Epub 2009 Jan 11. PMID: 19137006; PMCID: PMC2775068.

PubMed ID: 19137006