Cross Metathesis Route in Sphingomyelin Synthesis

Hasegawa, Hiroko; Yamamoto, T.; Hatano, Sho; Hakogi, Toshikazu; Katsumura, Shigeo

doi:10.1246/cl.2004.1592

Cited by 25 publications

(5 citation statements)

References 16 publications

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“…Recognising that variation in the sphingosine and fatty acid alkyl chains could be introduced by simple cross metathesis and amine acylation respectively, 46 the problem simplified to generation of a set of core hydroxybutenyl amine scaffolds, which in turn could be accessed from readily available a-amino acids, Scheme 1. [26][27][28][29][30][31][32][33][34] Scheme 1 Retrosynthetic Analysis of the common scaffold.…”

Section: Synthesis Of Ceramide Analogue Librarymentioning

confidence: 99%

Exploring Leishmania major Inositol Phosphorylceramide Synthase (LmjIPCS): Insights into the ceramide binding domain

et al. 2011

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The synthesis of set of ceramide analogues exploring hydrophobicity in the acyl chains and the degree and nature of hydroxylation is described. These have been assayed against the parasitic protozoan enzyme LmjIPCS. These studies showed that whilst the C-3 hydroxyl group was not essential for turnover it provided enhanced affinity. Reflecting the membrane bound nature of the enzyme a long (C 13 ) hydrocarbon ceramide tail was necessary for both high affinity and turnover. Whilst the N-acyl chain also contributed to affinity, analogues lacking the amide linkage functioned as competitive inhibitors in both enzyme and cell-based assays. A model that accounts for this observation is proposed.

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Section: Synthesis Of Ceramide Analogue Librarymentioning

confidence: 99%

Exploring Leishmania major Inositol Phosphorylceramide Synthase (LmjIPCS): Insights into the ceramide binding domain

et al. 2011

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“…Conjugation to protein may be achieved by either elaboration of the terminal alkene, for example via the photoaddition of cysteamine and subsequent reaction of the resulting amine, or by installation of a suitably functionalized N ‐acyl group after reduction of the azide function. We and others have demonstrated that such truncated molecules may be efficiently elaborated to the full‐length sphingosines by olefin cross metathesis 55–58…”

Section: Resultsmentioning

confidence: 99%

Chemical and Chemoenzymatic Synthesis of S‐Linked Ganglioside Analogues and Their Protein Conjugates for Use as Immunogens

Rich

Wakarchuk

Bundle

2006

Chemistry A European J

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Analogues of the tumor-associated gangliosides GM(3) and GM(2) containing terminal S-linked neuraminic acid residues and an amino terminated, truncated ceramide homologue have been synthesized and conjugated to a protein. The synthesis involved coupling of a S-linked sialyl alpha(2-->3) galactose disaccharide with a glucosyl sphingosine analogue, followed by elaboration and deprotection to give amino-terminated glycosyl ceramide 1. Glycosyltransferase-catalyzed extension of the trisaccharide 1 provided access to the modified GM(2) tetrasaccharide 2 or sulphur-containing GD(3) analogue 30. Owing to their potentially enhanced resistance to endogenous exo-glycoside hydrolases and their inherent non-self character, carbohydrate antigens containing non-reducing terminal thioglycosidic linkages may be more immunogenic than O-linked antigens and may stimulate the production of antibodies capable of recognizing naturally occurring oligosaccharides. Our initial results suggest that in fact these antigens are viable immunogens and furthermore, that immune sera cross reacts with O-gangliosides in the context of a heterologous glycoprotein conjugate.

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“…Reductions with L-selectride and NaBH 4 gave 5 : 3 and 1 : 2 mixtures, respectively. 63,64 Oxidation of allyl amines Epoxidation Oxidation of amino acid derived allyl alcohols with mCPBA were studied by Ohfune and Sakai during their synthesis of galantin I (Scheme 52). High selectivity was obtained for substrates with Z-configuration (204, 210).…”

Section: Reduction Of Ynonesmentioning

confidence: 99%