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1-Deoxysphingosine (m18:1(14Z))

(Synonyms: 1-deoxySO, 14Z-1-Deoxysphingosine (d18:1)) 目录号 : GC41544

An atypical sphingolipid

1-Deoxysphingosine (m18:1(14Z)) Chemical Structure

Cas No.:2190487-94-4

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500μg
¥2,399.00
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1mg
¥4,078.00
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Sample solution is provided at 25 µL, 10mM.

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产品描述

1-Deoxysphingosine (m18:1(14Z)) is an atypical sphingolipid that contains a double bond at the n-4 (14Z) native position and is formed when serine palmitoyltransferase condenses palmitoyl-CoA with alanine instead of serine during sphingolipid synthesis. It lacks the C1-hydroxyl group necessary for canonical degradation, however, it is metabolized by the cytochrome P450 (CYP) subfamilies CYP4A and CYP4F in MEF cells.

Chemical Properties

Cas No. 2190487-94-4 SDF
别名 1-deoxySO, 14Z-1-Deoxysphingosine (d18:1)
Canonical SMILES C[C@H](N)[C@H](O)CCCCCCCCCC/C=C\CCC
分子式 C18H37NO 分子量 283.5
溶解度 DMF: 10 mg/ml,DMSO: 2 mg/ml,Ethanol: miscible 储存条件 Store at -20°C
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1 mM 3.5273 mL 17.6367 mL 35.2734 mL
5 mM 0.7055 mL 3.5273 mL 7.0547 mL
10 mM 0.3527 mL 1.7637 mL 3.5273 mL
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Research Update

Elucidating the chemical structure of native 1-deoxysphingosine

J Lipid Res 2016 Jul;57(7):1194-203.PMID:27165858DOI:PMC4918849

The 1-deoxysphingolipids (1-deoxySLs) are formed by an alternate substrate usage of the enzyme, serine-palmitoyltransferase, and are devoid of the C1-OH-group present in canonical sphingolipids. Pathologically elevated 1-deoxySL levels are associated with the rare inherited neuropathy, HSAN1, and diabetes type 2 and might contribute to β cell failure and the diabetic sensory neuropathy. In analogy to canonical sphingolipids, it was assumed that 1-deoxySLs also bear a (4E) double bond, which is normally introduced by sphingolipid delta(4)-desaturase 1. This, however, was never confirmed. We therefore supplemented HEK293 cells with isotope-labeled D3-1-deoxysphinganine and compared the downstream formed D3-1-deoxysphingosine (1-deoxySO) to a commercial synthetic SPH m18:1(4E)(3OH) standard. Both compounds showed the same m/z, but differed in their RPLC retention time and atmospheric pressure chemical ionization in-source fragmentation, suggesting that the two compounds are structural isomers. Using dimethyl disulfide derivatization followed by MS(2) as well as differential-mobility spectrometry combined with ozone-induced dissociation MS, we identified the carbon-carbon double bond in native 1-deoxySO to be located at the (Δ14) position. Comparing the chromatographic behavior of native 1-deoxySO to chemically synthesized SPH m18:1(14Z\) and (14E) stereoisomers assigned the native compound to be SPH m18:1(14Z\). This indicates that 1-deoxySLs are metabolized differently than canonical sphingolipids.