860493P

Avanti

1-deoxysphinganine

1-deoxysphinganine (m18:0), powder

Empirical Formula (Hill Notation):
C18H39NO
CAS Number:
Molecular Weight:
285.51
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 1 mg (860493P-1mg)
pkg of 1 × 10 mg (860493P-10mg)

manufacturer/tradename

Avanti Polar Lipids 860493P

shipped in

dry ice

storage temp.

−20°C

SMILES string

C[C@@](N)([H])[C@]([H])(O)CCCCCCCCCCCCCCC

General description

1-deoxysphinganine is synthesized by the condensation of palmitic acid with alanine or glycine in the presence of enzyme serine palmitoyltransferase (SPT). It is metabolized to 1-deoxyceramides.

Application

1-deoxysphinganine may be used for the complex preparation with bovine serum albumin for cytotoxicity testing in MN9D dopaminergic neuroblastoma cell line. It is also suitable for use as a neurotoxic agent in human CD8+ T cells.

Biochem/physiol Actions

1-deoxysphinganine elicits cytotoxicity towards dorsal root ganglion (DRG) neurons by disrupting the neuronal cytoskeleton formation. High levels of 1-deoxysphinganine in diabetic patients may contribute to the reduction of pancreatic β cell functionality. In hereditary sensory and autonomic neuropathy type I, mutation in the serine palmitoyltransferase gene results in altered substrate specificity, resulting in the accumulation of 1-deoxysphinganine.

Packaging

5 mL Amber Glass Screw Cap Vial (860493P-1mg)
5 mL Amber Glass Screw Cap Vial (860493P-10mg)

RIDADR

NONH for all modes of transport

Certificate of Analysis

Certificate of Origin

Deoxysphingolipids, novel biomarkers for type 2 diabetes, are cytotoxic for insulin-producing cells
Zuellig RA, et al.
Diabetes, 63(4), 1326-1339 (2014)
Loss of Neurological Disease HSAN-I-Associated Gene SPTLC2 Impairs CD8+ T Cell Responses to Infection by Inhibiting T Cell Metabolic Fitness
Wu J, et al.
Immunity, 50(5), 1218-1231 (2019)
M F Dohrn et al.
European journal of neurology, 22(5), 806-814 (2015-01-28)
Diabetic distal sensorimotor polyneuropathy (DSPN) is a frequent, disabling complication of diabetes mellitus. There is increasing evidence that sphingolipids play a role in insulin resistance and type 2 diabetes (T2DM). Whether neurotoxic 1-deoxy-sphingolipids are elevated in DSPN patients' plasma and...
Elucidating the chemical structure of native 1-deoxysphingosine
Steiner R, et al.
Journal of Lipid Research, 57(7), 1194-1203 (2016)
Irina Alecu et al.
Journal of lipid research, 58(1), 60-71 (2016-11-23)
The 1-deoxysphingolipids (1-deoxySLs) are atypical sphingolipids (SLs) that are formed when serine palmitoyltransferase condenses palmitoyl-CoA with alanine instead of serine during SL synthesis. The 1-deoxySLs are toxic to neurons and pancreatic β-cells. Pathologically elevated 1-deoxySLs cause the inherited neuropathy, hereditary...

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