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Usage

Uses

Used in Pharmaceutical Industry:
1-O-β-D-Glucopyranosyl-N-hexadecanoylsphingosine is used as a therapeutic target for the treatment of metabolic disorders, neurodegenerative diseases, and cancer. Its dysregulation has been linked to these diseases, making it a promising candidate for drug development and intervention.
Used in Research Applications:
1-O-β-D-Glucopyranosyl-N-hexadecanoylsphingosine is used as a research tool for studying cell signaling, membrane structure, and intracellular trafficking. Its involvement in various physiological processes makes it an important molecule for understanding cellular functions and mechanisms.
Used in Drug Delivery Systems:
1-O-β-D-Glucopyranosyl-N-hexadecanoylsphingosine can be used as a component in drug delivery systems to improve the targeting and efficacy of therapeutic agents. Its presence in cell membranes and its role in cellular processes make it a potential carrier for drug delivery.

Upstream product

• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 112-71-0 1-Bromotetradecane 
• 103348-49-8 2-azido-sphingosine 
• 108283-57-4 (2S,3R,4E)-2-azido-1-(triphenylmethyl)-4-octadecene-1,3-diol 
• 25791-20-2 (n-tetradecyl)triphenylphosphonium bromide 
• 108283-58-5 (2S,3R,4E)-2-azido-3-benzoyl-1-(triphenylmethyl)-4-octadecene-1,3-diol 
• 1492-30-4 4-nitrophenyl palmitate 
• 4201-55-2 (2S,3R,4E)-3-benzoyl-2-(hexadecanamido)-4-octadecene-1,3-diol 
• 143517-08-2 1-OTBDPS ceramide 
• 143517-09-3 Benzoic acid (E)-(R)-1-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-hexadecanoylamino-ethyl]-hexadec-2-enyl ester 
• 1535186-22-1 (2S,3R,4E)-2-(tetrachlorophthalimido)-1-O-(t-butyldiphenylsilyl)-4-octadecen-1,3-diol 
• 94069-97-3 Hexadecanoic acid ((E)-(1S,2R)-2-hydroxy-1-trityloxymethyl-heptadec-3-enyl)-amide 
• 4201-55-2 Benzoic acid (E)-(S)-1-((R)-1-hexadecanoylamino-2-hydroxy-ethyl)-hexadec-2-enyl ester 
• 172340-52-2 Benzoic acid (E)-(R)-1-[(S)-1-azido-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester 

Relevant academic research and scientific papers

Total synthesis of ceramides and β-O-glucosylceramides via intramolecular fatty acyl group migration

Acyl migration of alkyl and aromatic acyl groups from an alcohol to another alcohol or amine is a phenomenon that occurs in nature and can be a bane to some synthetic strategies. An acyl migration-dependent method was developed for the synthesis of ceramide and glucosyl ceramide derivatives, in which the desired fatty acyl moiety acts both as protecting and migrating group. Removal of the tetrachlorophthalimido (TCP) group with ethylenediamine as a mild base at room temperature resulted in subsequent intramolecular fatty acyl group migration from -O to -N, on sphingosine or per acetylated glucosyl sphingosine to yield the desired N-acylated products. Deacetylation reaction afforded the desired β-O-glucosylceramide derivatives. Thus, choice of the appropriate blocking group turns acyl migration into a tool for synthesis, rather than an impediment.

Borinic acid-catalyzed stereo- and site-selective synthesis of β-glycosylceramides

A method for activation of unprotected ceramides towards stereo- and site-selective glycosylation is described. Two-point binding of a diarylborinic acid catalyst to the ceramide accelerates its reactions with 'armed' glycosyl methanesulfonate donors, resulting in the formation of a β-glycosidic linkage at the primary OH group.

Synthesis of a panel of carbon-13-labelled (glyco)sphingolipids

The synthesis of a focussed library of sphingolipids differing in the number and position of 13C labels is described. The synthesised sphingolipids differ in substitution at both the sphingosine amine (either palmitoylated or unmodified) and the sphingosine primary hydroxyl (unmodified or glycosylated). Moreover, 13C atoms are incorporated into either the sphingosine or the palmitate moiety, or both. This set of compounds is intended for use in relative quantitative lipidomics studies to gain insight into sphingolipid metabolism in healthy and diseased (lysosomal storage disorders) patients and animal models. The synthesis of a focussed library of sphingolipids differing in the number and position of 13C labels is described. 13C atoms are incorporated into either the sphingosine or the palmitate moiety, or both. This set of compounds is intended for use in relative quantitative lipidomics studies to gain insight into sphingolipid metabolism.

Efficient syntheses of a series of glycosphingolipids with 1,2-trans-glycosidic linkages

A series of glycosphingolipids with 1,2-trans-glycosidic linkages were synthesized in the presence of neighboring group participation using trichloroacetimidates as glycosyl donors and an azido-sphingosine as the glycosyl acceptor. During the preparation

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.

Syntheses of two pairs of enantiomeric C18-sphingosines and a palmitoyl analogue of gaucher spleen glucocerebroside

Sixteen kinds of chiral C4-epoxides [(-)-10a-d,(+)-10a-d,(-)-11a-d,(+)-11a-d], which are synthons in our synthetic strategy for complex lipids, have been prepared from (2Z)-2-butene-1,4-diol (6) by employing a Sharpless asymmetric epoxidation. By using the chiral C4-epoxides [(+)-10a,(-)-10a,(-)-11a,(+)-11a] as starting compounds, two pairs of enantiomeric (D-erythro, L-erythro, D-threo, and L-threo)-C18-sphingosines (1, 2, 3, 4) have been synthesized via a regioselective ring-opening of the epoxide ring with azide anion followed by reduction of the azide group to an amino group and a Wittig reaction. Furthermore, D-erythro-C18-sphingosine (1) has been converted to a palmitoyl analogue (5a) of Gaucher spleen glucocerebroside (5) through a reaction pathway including successive condensations with palmitic acid and D-glucose.