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860477P

Avanti

1-desoxymethylsphingosine

1-desoxymethylsphingosine (m17:1), powder

Synonym(s):

1-Deoxymethylsphingosine

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About This Item

Empirical Formula (Hill Notation):
C17H35NO
CAS Number:
1246303-16-1
Molecular Weight:
269.47
MDL number:
MFCD22416651
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 1 mg (860477P-1mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860477P

lipid type

sphingolipids
bioactive lipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCC/C=C/[C@](O)([H])CN

InChI

1S/C17H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17(19)16-18/h14-15,17,19H,2-13,16,18H2,1H3/b15-14+/t17-/m1/s1

InChI key

NTZGVZKEAIALQE-IAOULYHDSA-N

General description

1-desoxymethylsphingosine is synthesized from glycine in the presence of the enzyme serine palmitoyltransferase (SPT).[1]

Application

1-desoxymethylsphingosine may be used for the complex preparation with bovine serum albumin for cytotoxicity testing in MN9D dopaminergic neuroblastoma cell line.[2]

Biochem/physiol Actions

1-desoxymethylsphingosine is less neurotoxic compared to 1-desoxysphingosine in dorsal root ganglion neuronscultures[3] Mutations in the palmitoyltransferase (SPT) in hereditary sensory neuropathy type 1 (HSAN-1), due to altered substrate specificity 1-desoxymethylsphinganine and 1-deoxy-sphinganine which are further converted to -deoxy(methyl)-ceramide and 1-deoxy(methyl)-sphingosine (1-deoxy(methyl)-SO). However, they lack the hydroxyl group essential for glycosphingolipid generation, resulting in accumulation of intermediate products.[4]

Packaging

5 mL Amber Glass Screw Cap Vial (860477P-1mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

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1-Deoxysphingolipids encountered exogenously and made de novo: dangerous mysteries inside an enigma
Duan, Jingjing and Merrill, Alfred H
The Journal of Biological Chemistry, 290(25), 15380-15389 (2015)
Annelies Rotthier et al.
Human mutation, 32(6), E2211-E2225 (2011-05-28)
Hereditary sensory and autonomic neuropathy type I (HSAN-I) is an axonal peripheral neuropathy leading to progressive distal sensory loss and severe ulcerations. Mutations in SPTLC1 and SPTLC2, encoding the two subunits of serine palmitoyltransferase (SPT), the enzyme catalyzing the first
Hereditary sensory neuropathy type 1 is caused by the accumulation of two neurotoxic sphingolipids
Penno A, et al.
The Journal of Biological Chemistry, 285(15), 11178-11187 (2010)
Ceramide sphingolipid signaling mediates Tumor Necrosis Factor (TNF)-dependent toxicity via caspase signaling in dopaminergic neurons
Martinez TN, et al.
Mol. Neurodegener., 7(1), 45-45 (2012)
Anke Penno et al.
The Journal of biological chemistry, 285(15), 11178-11187 (2010-01-26)
HSAN1 is an inherited neuropathy found to be associated with several missense mutations in the SPTLC1 subunit of serine palmitoyltransferase (SPT). SPT catalyzes the condensation of serine and palmitoyl-CoA, the initial step in the de novo synthesis of sphingolipids. Here
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