860464P
Avanti
N-C24:1-deoxysphinganine
Avanti Polar Lipids 860464P, powder
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Synonym(s):
N-nervonoyl-1-deoxysphinganine (m18:0/24:1)
Empirical Formula (Hill Notation):
C42H83NO2
Recommended Products
form
powder
packaging
pkg of 1 × 1 mg (860464P-1mg)
manufacturer/tradename
Avanti Polar Lipids 860464P
lipid type
sphingolipids
bioactive lipids
shipped in
dry ice
storage temp.
−20°C
SMILES string
C[C@]([H])(NC(CCCCCCCCCCCCC/C=C\CCCCCCCC)=O)[C@]([H])(O)CCCCCCCCCCCCCCC
General description
1-deoxysphinganine is an atypical sphingoid base, which lacks a 1-hydroxyl group.
Application
N-C24:1-deoxysphinganine or N-nervonoyl-1-deoxysphinganine (m18:0/24:1) has been used as a standard in the quantitation of atypical sphingoid bases in biological samples by reverse-phase liquid chromatography coupled to electrospray ionization tandem mass spectrometry (LC-MS/MS).
Biochem/physiol Actions
1-deoxysphinganine might be toxic to cancer cells. It is a potential biomarker for type 2 diabetes. 1-deoxysphinganine acts as a cytotoxic lipid for insulin producing cells.
Packaging
5 mL Amber Glass Screw Cap Vial (860464P-1mg)
WGK
WGK 3
Certificates of Analysis (COA)
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Deoxysphingolipids, novel biomarkers for type 2 diabetes, are cytotoxic for insulin-producing cells.
Richard A Zuellig et al.
Diabetes, 63(4), 1326-1339 (2014-01-01)
Irreversible failure of pancreatic β-cells is the main culprit in the pathophysiology of diabetes, a disease that is now a global epidemic. Recently, elevated plasma levels of deoxysphingolipids, including 1-deoxysphinganine, have been identified as a novel biomarker for the disease.
Junliang Wan et al.
Journal of agricultural and food chemistry, 67(46), 12953-12961 (2019-10-23)
Most common sphingolipids are comprised of "typical" sphingoid bases (sphinganine, sphingosine, and structurally related compounds) and are produced via the condensation of l-serine with a fatty acyl-CoA by serine palmitoyltransferase. Some organisms, including mammals, also produce "atypical" sphingoid bases that
Noemi Jiménez-Rojo et al.
Biophysical journal, 107(12), 2850-2859 (2014-12-18)
Ceramides and dihydroceramides are N-acyl derivatives of sphingosine and sphinganine, respectively, which are the major sphingoid-base backbones of mammals. Recent studies have found that mammals, like certain other organisms, also produce 1-deoxy-(dihydro)ceramides (1-deoxyDHCers) that contain sphingoid bases lacking the 1-hydroxyl-
Sarah T Pruett et al.
Journal of lipid research, 49(8), 1621-1639 (2008-05-24)
"Sphingosin" was first described by J. L. W. Thudichum in 1884 and structurally characterized as 2S,3R,4E-2-aminooctadec-4-ene-1,3-diol in 1947 by Herb Carter, who also proposed the designation of "lipides derived from sphingosine as sphingolipides." This category of amino alcohols is now
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