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
Molecular Weight
252.392
Exact Mass
252.209
Synonyms
<p>aPA</p>
Tallman, K.A., M.D. Armstrong, S.B. Milne, L.J. Marnett, H.A. Brown, and N.A. Porter. (2013). Cobalt carbonyl complexes as probes for alkyne-tagged lipids. J Lipid Res 54:859-68. [PubMed] Milne, S.B., K.A. Tallman, R. Serwa, C.A. Rouzer, M.D. Armstrong, L.J. Marnett, C.M. Lukehart, N.A. Porter, and H.A. Brown. (2010). Capture and release of alkyne-derivatized glycerophospholipids using cobalt chemistry. Nat Chem Biol 6:205-207. [PubMed] Jiang, H., S. Khan, Y. Wang, G. Charron, B. He, C. Sebastian, J. Du, R. Kim, E. Ge, R. Mostoslavsky, H.C. Hang, Q. Hao, and H. Lin. (2013). SIRT6 regulates TNF-alpha secretion through hydrolysis of long-chain fatty acyl lysine. Nature 496:110-3. [PubMed] Thiele, C., C. Papan, D. Hoelper, K. Kusserow, A. Gaebler, M. Schoene, K. Piotrowitz, D. Lohmann, J. Spandl, A. Stevanovic, A. Shevchenko, and L. Kuerschner. (2012). Tracing fatty acid metabolism by click chemistry. ACS Chem Biol 7:2004-11. [PubMed] Gao, X., N. Arenas-Ramirez, S.J. Scales, and R.N. Hannoush. (2011). Membrane targeting of palmitoylated Wnt and Hedgehog revealed by chemical probes. FEBS Lett 585:2501-6. [PubMed] Yap, M.C., M.A. Kostiuk, D.D. Martin, M.A. Perinpanayagam, P.G. Hak, A. Siddam, J.R. Majjigapu, G. Rajaiah, B.O. Keller, J.A. Prescher, P. Wu, C.R. Bertozzi, J.R. Falck, and L.G. Berthiaume. (2010). Rapid and selective detection of fatty acylated proteins using omega-alkynyl-fatty acids and click chemistry. J Lipid Res 51:1566-80. [PubMed] Martin, B.R. and B.F. Cravatt. (2009). Large-scale profiling of protein palmitoylation in mammalian cells. Nat Methods 6:135-8. [PubMed]