94198-71-7Relevant academic research and scientific papers
NOVEL SYNTHESIS INTERMEDIATES FOR OBTAINING DERIVATIVES OF SPHINGOSINES, CERAMIDES AND SPHINGOMYELINS WITH GOOD YIELDS
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Paragraph 0093; 0094; 0095, (2016/04/19)
The subject matter of the present invention is the novel molecules of formulae E, E′ and F. These molecules prove to be synthesis intermediates that are very advantageous for the manufacture of derivatives of sphingosine or of ceramides functionalized in position 1, with good yields, in which R1 and R2 are fatty chains, R3 is an alkyl group and R4 is a protective group for alcohol functions. Another subject of the invention is the use of the intermediates of type F for converting same into intermediates of type G, by means of reduction in the presence of lithium borohydride. The G molecules are precursors that are known to make it possible to obtain sphingolipids or sphingomyelin.
METHODS FOR THE SYNTHESIS OF SPHINGOMYELINS AND DIHYDROSPHINGOMYELINS
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Paragraph 00236; 00237, (2014/09/29)
The present invention includes methods for the synthesis of sphingomyelins and dihydrosphingomyelins. The present invention also includes methods for the synthesis of sphingosines and dihydrosphingosines. The present invention further includes methods for the synthesis of ceramides and dihydroceramides.
METHODS FOR THE SYNTHESIS OF SPHINGOMYELINS AND DIHYDROSPHINGOMYELINS
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Paragraph 0298, (2014/09/30)
The present invention includes methods for the synthesis of sphingomyelins and dihydrosphingomyelins. The present invention also includes methods for the synthesis of sphingosines and dihydrosphingosines. The present invention further includes methods for the synthesis of ceramides and dihydroceramides.
The relationship between the structure of the headgroup of sphingolipids and their ability to form complex high axial ratio microstructures
Goldstein, Alex S,Gelb, Michael H,Yager, Paul
, p. 1 - 14 (2007/10/03)
Ceramides with chemically modified polar headgroups were prepared and examined for their ability to form complex high axial ratio microstructures (CHARMS), potential drug delivery vehicles. In general, if the modified ceramide had either a hydrogen bond donor or acceptor at C-1 and C-3, including hydrophobic or hydrophilic groups attached to C-1 microstructures formed. Tolerated groups include amides, esters, sulfonates, and ethers. If modification at C-3 added significant bulk (greater than four carbons regardless of hydrophilicity), then amorphous aggregates formed. Ceramides with C-1 and C-3 bridged through a cyclic structure also made microstructures. By using a sphingolipid with an amine headgroup, CHARMs may be modified covalently after formation.
The total synthesis of ganglioside GM3
Duclos Jr., Richard I.
, p. 489 - 507 (2007/10/03)
Previous syntheses of ganglioside GM3 (NeuAcα3Galβ4Glcβ1Cer) are reviewed, and both chemoenzymatic and chemical total synthetic approaches were investigated. In a chemoenzymatic approach, (2S,3R,4E)-5'''-acetyl-α-neuraminyl-(2''' → 3'')-β-galactopyranosyl-(1'' → 4')-β-glucopyranosyl-(1' mutually implies 1)-2-azido-4-octadecene-1,3-diol (azidoGM3) was readily prepared utilizing recombinant β-Gal-(1'' → 3'/4')-GlcNAc α-(2''' → 3'')-sialyltransferase enzyme, and was evaluated as a synthetic intermediate to ganglioside GM3. The chemical total synthesis of ganglioside GM3 was performed on one of the largest scales yet reported. The highlights of this synthesis include minimizing the steps necessary to prepare the lactosyl acceptor as a useful anomeric mixture, which was present in excess for the highly regioselective and fairly stereoselective sialylation with a known neuraminyl donor to give the protected GM3 trisaccharide. The synthetic methodology maximized convergence by a subsequent glycosidic coupling of the well-characterized GM3 trisaccharide trichloroacetimidate derivative with protected ceramide. The ganglioside GM3 was nearly homogeneous as the two glycosidic couplings utilized preparative HLPC purifications, and variations in the sphingosine base and fatty acyl group were under 0.1 and 0.2%, respectively. (C) 2000 Elsevier Science Ltd.
