52050-17-6

Usage

Uses

Used in Medical Research:
GLUCOPSYCHOSINE is used as a biomarker for the identification of lipids that rapidly and reversibly alter transepithelial electrical resistance (TER) or tight junction (TJ) permeability in epithelial tissue. This application aids in understanding the underlying mechanisms of various diseases and conditions affecting epithelial tissues.
Used in Gaucher Disease Diagnostics:
GLUCOPSYCHOSINE is used as an internal standard for the quantification of glucosyl sphingosine in Gaucher patients. This application is crucial for the accurate diagnosis and monitoring of Gaucher disease, a genetic disorder characterized by the accumulation of glucosylceramide in various tissues.
Used in Liquid Chromatography Electrospray Ionization Tandem Mass Spectrometric (LC/ESI-MS/MS):
GLUCOPSYCHOSINE is used as an internal standard in LC/ESI-MS/MS for the quantification of lysoglucosylceramide in plasma. This application is essential for the diagnosis and management of Gaucher disease, as it helps in measuring the levels of lysoglucosylceramide, a biomarker for the disease.
Used in Preeclampsia Research:
GLUCOPSYCHOSINE is used as a sphingosine derivative and a sphingolipid compound found in the umbilical cord artery of women with preeclampsia. This application helps in understanding the role of GLUCOPSYCHOSINE in the development of preeclampsia and its potential as a therapeutic target.
Used in Liquid Chromatography with Tandem Mass Spectrometry (LC-MS/MS):
GLUCOPSYCHOSINE is used in LC-MS/MS for the quantification of lysoglucosylceramide in plasma for Gaucher disease. This application is vital for the accurate measurement of lysoglucosylceramide levels, which can help in the diagnosis and treatment of Gaucher disease.

Biochem/physiol Actions

Glucosyl?sphingosine is a potential biomarker for Gaucher′s?disease.?It modulates?Ca2+?release?in the brain?microsomes.

InChI:InChI=1/C24H47NO7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)18(25)17-31-24-23(30)22(29)21(28)20(16-26)32-24/h14-15,18-24,26-30H,2-13,16-17,25H2,1H3/b15-14+/t18?,19-,20-,21-,22+,23+,24-/m1/s1

Upstream product

• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 112-71-0 1-Bromotetradecane 
• 103348-50-1 (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 114275-39-7 (2R,3R,4E)-1,3-benzylidene-4-octadecene-1,2,3-triol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 131105-37-8 (2S,3R,4E)-3-O-benzoyl-N-trifluoroacetyl-1-O-trityl-4-sphingenine 
• 131105-36-7 (2S,3R,4E)-N-trifluoroacetyl-1-O-trityl-4-sphingenine 
• 18459-13-7 (2S,3R,4E)-3-O-benzoyl-N-trifluoroacetyl-4-sphingenine 
• 130967-71-4 N-[(2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl]-2,2,2-trifluoroacetamide 
• 103366-74-1 2,3,4,6-Tetra-O-pivaloyl-α-D-glucopyranosyl trichloroacetimidate 
• 108283-59-6 (2S,3R,4E)-2',3',4',6'-tetraacetyl-β-D-glucopyranosyl-(1'<->1)-2-azido-3-benzoyl-4-octadecene-1,3-diol 
• 25791-20-2 (n-tetradecyl)triphenylphosphonium bromide 
• 108283-57-4 (2S,3R,4E)-2-azido-1-(triphenylmethyl)-4-octadecene-1,3-diol 

Downstream Products

• 36271-49-5 (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(octadecanoylamino)-3-hydroxyoctadec-4-ene 
• 35823-61-1 N-Acetylpsychosine 
• 41613-16-5 C₃₂H₆₁NO₈ 
• 73039-25-5 erythro-N-oleoyl-1-O-β-D-galactosyl-D-sphingosine 
• 173067-83-9 4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-2-dichloroacetamido-4-octadecen-1,3-diol 
• 173067-85-1 2,3-di-O-benzoyl-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol 
• 173067-86-2 2,3,6-tri-O-benzoyl-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol 
• 173067-84-0 2,3-di-O-benzoyl-4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol 
• 173067-87-3 2,3,6-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol 
• 173067-88-4 S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-benzoyl-4-thio-β-D-glucopyranosyl-(1<*>1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol 
• 88035-98-7 2-Hydroxy-N-[(E)-2-hydroxy-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadec-3-enyl]-malonamic acid tetradecyl ester 
• 74365-77-8 glucosylceramide 
• 34324-89-5 (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(hexadecanoylamino)-3-hydroxyoctadec-4-ene 
• 17283-91-9 (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(15(Z)-tetracosenoylamino)-3-hydroxyoctadec-4-ene 

Relevant academic research and scientific papers

3-O-SULFO-GALACTOSYLCERAMIDE ANALOGS AS ACTIVATORS OF TYPE II NKT CELLS AND USES THEREOF

Disclosed is a compound of the formula (I) or (II): wherein a f are as described herein. The compounds are useful in the activation of Type II NKT cells and in treating cancer.

Glycosynthase mediated synthesis of psychosine

Globoid cell leukodystrophy (GCL), or Krabbe disease, is a lysosomal storage disorder characterized by a deficiency in galactosylceramidase (GALC), which hydrolyses galactosylceramide and galactosylsphingosine (psychosine). Early detection of GCL in newborns is essential for timely therapeutic intervention and could be achieved by testing infant blood samples with isotopically labeled lysosmal enzyme substrates and mass spectrometry. While isotopically labeled psychosine would be a useful tool for the early diagnosis of GCL, its synthesis is lengthy and expensive. To obviate this problem we developed a one-step chemoenzymatic synthesis of psychosine using a glycosynthase mutant of the Rhodococcus equi endogalactosylceramidase (EGALC), α-D-galactopyranosyl fluoride and sphingosine.

Synthesis and biological evaluation of antifungal activities of novel 1,2-trans glycosphingolipids

The synthesis and in-vitro biological evaluation of antifungal activities of a series of 1,2-trans glycosphingolipids (GSL) against Candida albicans, Candida parapsilosis, and Candida tropicalis were described. The preliminary study indicated that the sor

The total syntheses of D-erythro-sphingosine, N-palmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog

The total synthesis of D-erythro-sphingosine (9) was performed by a chirospecific method starting from D-galactose via an azidosphingosine intermediate to give highly homogeneous ( > 99.9% C18:1) sphingosine base (9) which contained no observable olefin isomerization by product and was demonstrated to be optically pure by a novel method utilizing Mosher's acid. Ceramide (10) was prepared from this sphingosine (9) with highly homogeneous (99.8% C16:0) palmitic acid by two methods. The cerebroside glucosylceramide (23) was the next sphingolipid in this series to be synthesized in a highly homogeneous form. These three sphingolipids are currently being used for biophysical studies of the structures of their hydrated bio-molecular assemblies.

Synthesis of Sphingosine Relatives, IX. Synthesis of (2S,3R,4E)-1-O-(β-D-Glucopyranosyl)-N--4-sphingenine. The Structure Proposed for the Esterified Cerebroside in the Epidermis of Guinea Pigs

(2S,3R,4E)-1-O-(β-D-Glucopyranosyl)-N--4-sphingenine (1) was synthesized from D-glucose (A), (2S,3R,4E)-4-sphingenine (sphingosine, B), 24-hydroxytetracosanoic acid (C) and linoleic acid (D).The 1H-NMR spectrum of the synthetic 1 was different from that of the esterified cerebroside which was isolated as a tissue-characteristic compound in the epidermis of foodpad and dorsal skin of guinea pigs.

Process for the preparation of sphingosine derivatives

The invention relates to a new process for the preparation of the sphingosine derivatives described in European Patent Application No. 146,810, of the formula: STR1 It comprises protecting D-galactose in the 4,6-position and oxidizing it to the corresponding D-threose protected in the 2,4-position, condensing an aliphatic chain (R3) onto the latter by a Wittig reaction, converting the free hydroxyl group into a azido group and splitting off the protective group, protecting the resulting 2-azido-1,3-dihydroxy compound selectively in the 1-position and blocking it in the 3-position, liberating the 1-hydroxy group again, glycosidating the resulting compound or the abovementioned 2-azido-1,3-dihydroxy compound with the 0-trifluoro- or 0-trichloro-acetimade or the 1-halogen derivative of a 2,3,4,6-0-tetraacyl-D-glucose, splitting off the acyl groups of these and the protective group in the 3-position, converting the azido group into an amino group and acylating the amino compound with a fatty acid R1 --OH. The process gives the compounds of the therapeutically more active D series in a high yield in relatively few stages without resolving diastereomers.

Pyridinecarboxamide or trimethoxybenzamide compounds derived from nitrogenous lipids, pharmaceutical compositions containing same which possess anti-convalsive and anti-epileptic properties

Organic amide compounds of the formula STR1 wherein R1 --CO is a residue of a carboxylic acid with the proviso that the carboxylic acid is not a natural fatty acid normally bound to nitrogen of nitrogenous lipids, R2 is a hydrogen atom, a C1-7 alkyl group, or a C4-7 cycloalkyl group, and R3-N is a residue of a nitrogenous lipid. The compounds are useful in increasing or stimulating the in vivo biological activity of in vitro biologically active carboxylic acids.