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860493P

Avanti

1-deoxysphinganine

Avanti Polar Lipids 860493P, powder

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Synonym(s):
1-deoxysphinganine (m18:0)
Empirical Formula (Hill Notation):
C18H39NO
CAS Number:
196497-48-0
Molecular Weight:
285.51
UNSPSC Code:
12352211
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

lipid type

bioactive lipids
sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

InChI

1S/C18H39NO/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18(20)17(2)19/h17-18,20H,3-16,19H2,1-2H3/t17-,18+/m0/s1

InChI key

YRYJJIXWWQLGGV-ZWKOTPCHSA-N

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Elucidating the chemical structure of native 1-deoxysphingosine
Steiner R, et al.
Journal of Lipid Research, 57(7), 1194-1203 (2016)
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
Mirthe Muilwijk et al.
BMJ open diabetes research & care, 8(1) (2020-05-08)
People of South Asian origin are at high risk of type 2 diabetes (T2D), but the underpinning mechanisms are not fully understood. We determined ethnic differences in acylcarnitine, amino acid and sphingolipid concentrations and determined the associations with T2D. Associations
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