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Synthesis and Evaluation of Sphinganine Analogues of KRN7000 and OCH
The Journal of Organic Chemistry, 2005[structures: see text] The phytosphingosine-containing alpha-galactosylceramides (alpha-GalCers), KRN7000 and OCH, have been shown to activate NKT cells via interaction with CD1d, a member of the CD1 family of antigen presenting proteins. Evidence from KRN7000 stimulation of NKT cells suggests that alpha-GalCers may have applications in the treatment ...
Rachel M, Ndonye +8 more
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ChemInform Abstract: Synthesis of Fluorinated Sphinganine and Dihydroceramide Analogues.
ChemInform, 2001AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Steven De Jonghe +6 more
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J. Chem. Soc., Perkin Trans. 1, 1986
(Z)-1-Trichloroacetimidoyloxyoctadec-2-ene, easily obtained from (Z)-octadec-2-en-1-ol, was iodocyclized with N-iodosuccinimide to give the 4-(1-iodohexadecyl)-2-trichloromethyl-4,5-dihydro-oxazole. From this compound, two routes were developed, either to pure (±)-erythro-sphinganine triacetate or to pure (±)-threo-sphinganine triacetate, respectively.
Alessandro Bongini +4 more
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(Z)-1-Trichloroacetimidoyloxyoctadec-2-ene, easily obtained from (Z)-octadec-2-en-1-ol, was iodocyclized with N-iodosuccinimide to give the 4-(1-iodohexadecyl)-2-trichloromethyl-4,5-dihydro-oxazole. From this compound, two routes were developed, either to pure (±)-erythro-sphinganine triacetate or to pure (±)-threo-sphinganine triacetate, respectively.
Alessandro Bongini +4 more
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Monolayer studies on derivatives of sphinganine and 4t-sphingenine
Chemistry and Physics of Lipids, 1974Abstract The pressure-area isotherms (π-A-isotherms) at temperatures between 4° and 47°C of the following derivatives of sphinganine and 4 t -sphingenine have been determined. N-palmitoyl-D,L-sphingenine (I), N-palmitoyl-diacetyl-D,L-sphingenine (II), N-acetyl-sphingenine (III), N-acetyl-D,L-erythro-sphinganine (IV), N-acetyl-D,L-threo-sphinganine ...
W. Stoffel, H.D. Pruss, G. Sticht
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ChemInform Abstract: STEREOSPECIFIC SYNTHESIS OF D‐THREO‐SPHINGANINE
Chemischer Informationsdienst, 1974AbstractL‐Serin (I) liefert die Phthaloylverbindung (IIa), die über das Säurechlorid (IIb) in das Diazoketon (III) übergeführt wird.
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Cancer Prevention Research, 2008
Abstract B102 Fenretinide (4-hydroxyphenylretinamide, 4HPR) is a promising anticancer agent that is being evaluated in human clinical trials. One of the proposed mechanisms of action for 4HPR is to increase the biosynthesis of ceramide, an inducer of apoptosis.
Kacee Sims +11 more
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Abstract B102 Fenretinide (4-hydroxyphenylretinamide, 4HPR) is a promising anticancer agent that is being evaluated in human clinical trials. One of the proposed mechanisms of action for 4HPR is to increase the biosynthesis of ceramide, an inducer of apoptosis.
Kacee Sims +11 more
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ChemInform Abstract: SYNTH. VON RACEMISCHEM 3‐DEHYDRO‐N‐BENZOYL‐SPHINGANIN
Chemischer Informationsdienst, 1973AbstractDie Hydroxymethylierung des Benzamidoheptadecanons (I) mit Formalin in Gegenwart von NaHCO3 in Äthanol‐Chloroform bei 38°C liefert das racemische Dehydrobenzoylsphinganin (II), eine biosynthetische Vorstufe der Sphingosin‐ Basen.
N. A. SOKOLOVA +3 more
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Tetrahedron, 2017
A diastereoselective route to the synthesis of D-threo-sphinganine, L-erythro-sphinganine and (−)-spisulosine from the higher homologue of Garner's aldehyde prepared from l-aspartic acid is reported. While the starting material contains one of the stereocenters in the target molecules, the other is generated by proline-catalyzed asymmetric α ...
Vipin Kumar Jain, Ramesh Ramapanicker
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A diastereoselective route to the synthesis of D-threo-sphinganine, L-erythro-sphinganine and (−)-spisulosine from the higher homologue of Garner's aldehyde prepared from l-aspartic acid is reported. While the starting material contains one of the stereocenters in the target molecules, the other is generated by proline-catalyzed asymmetric α ...
Vipin Kumar Jain, Ramesh Ramapanicker
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Synthesis of tritium labelled phosphonate analogues of sphinganine-1-phosphate
Journal of Labelled Compounds and Radiopharmaceuticals, 1997Tritiated phosphonate analogues 2 and 10 are prepared as analogues of sphinganine-1-phosphate 4. The key step in this synthesis is the catalytic tritiation of the triple bond in reduction of the protected diethyl-3-(S)-tert-butoxycarbonylamino-4-hydroxy-5-tridecinyl-1-phosphonate by means of sodium boro[ 3 H]hydride as tritium source.
Andreas Schick +3 more
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2007
Fumonisin B1 is structurally similar to sphinganine (Sa) and sphingosine (So) and inhibits ceramide synthase. It causes an elevation in Sa concentration, leading to an increase in Sa/So ratio in exposed animals. This increase often precedes fumonisins associated toxicity and that is why Sa/So ratio and free Sa have been proposed as biomarkers of ...
Bailly, J.D. +4 more
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Fumonisin B1 is structurally similar to sphinganine (Sa) and sphingosine (So) and inhibits ceramide synthase. It causes an elevation in Sa concentration, leading to an increase in Sa/So ratio in exposed animals. This increase often precedes fumonisins associated toxicity and that is why Sa/So ratio and free Sa have been proposed as biomarkers of ...
Bailly, J.D. +4 more
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