Synthesis of D-erythro-1-deoxydihydroceramide-1-sulfonic acid

Ohashi, Kinji; Yamagiwa, Yoshiro; Tadao, Kamikawaa; Kates, M.

doi:10.1016/s0040-4039(00)86683-6

Cited by 15 publications

(1 citation statement)

References 13 publications

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“…70 By chemical synthesis, the stereochemistry of the cysteinolic acid motif was shown to be d - erythro (2 R ,3 R ). 73,74 Although the biosynthesis of the sulfoceramides has not been studied, it may be proposed to occur by analogy with the well-studied biosynthesis of phosphoceramides. 75 A key question is whether the biosynthesis commences from l -serine, with a late introduction of the sulfonate group, or from l -cysteate.…”

Section: Cysteinolic Acid Conjugatesmentioning

confidence: 99%

Chemistry and biology of the aminosulfonate cysteinolic acid: discovery, distribution, synthesis and metabolism

Burchill

Williams

2022

Org. Biomol. Chem.

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Section: Cysteinolic Acid Conjugatesmentioning

confidence: 99%

Chemistry and biology of the aminosulfonate cysteinolic acid: discovery, distribution, synthesis and metabolism

Burchill

Williams

2022

Org. Biomol. Chem.

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Bacillariophyceae (Diatoms)

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: Frustules: Fundamental Characteristics of Diatoms Bases of Classification of Diatoms Primary Metabolites Photosynthetic Pigments Membrane Lipids Terpenic Hydrocarbons and Linear Polyunsaturated Alkenes Other Terpenic Derivatives: Description of the Two Biosynthetic Pathways Genera Nitzschia and Pseudo‐nitzschia : Domoic Acid and Analogs Other Molecules

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A Facile Stereoselective Synthesis of Sphingosine and Ceramide

Li¹,

Wu²

1996

Liebigs Ann./Recl.

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Flexible syntheses of sphingosine and ceramide were chain elongation with concomitant control of an E configuraachieved by using D-xylose as the chiral pool and a CuCNcatalyzed allylic alkylation reaction of a dimesylate 8 for tion of the double bond.By analogy with the central role of ceramide (1) in sphingolipid metabolism, ceramide plays an equally critical role as a second messenger in the sphingolipid-dependent pathway of cell signal transmission. Increase in ceramide levels may inhibit cell growth as a cellular defenselrepair mechanism and initiate apoptosis etc. Ceramide and diacylglycerol (DAG) may define opposing pathways of cell regulation [']. Moreover, sphingosine (2), the major constituent of ceramide, displays potent inhibiting properties of protein kinase C (PKC) both in vivo and in vitroL2] and thus plays a pivotal role in cell recognition, cell growth modulation and signal transmission. Glycosphingolipids derived from ceramide have also been shown to mediate cell recognition eventsL3].Harouse et al. recently demonstrated that galactosyl ceramide could act as a receptor for HIV binding in the cells lacking the CD4 receptor [4]. Therefore, owing to the ever increasing importance of sphingolipids and their metabolites in cell memberane research, the syntheses of their major constituent sphingosine and related compounds have received considerable attention and even more than 30 syntheses have been reported so far[536,71.The general consideration of sphingosine synthesis involves two aspects; one is the establishment of the chirality and the other the construction of the trans double bond. The introduction of the chirality from a chiral pool seemed to be particularly desirable and efficient. However, the required trans-selective C = C bond formation with simultaneous chain extension with a l k y n e~[~~*~~] or the WittigL5pp5'I method was not always satisfactory. A recent report on the synthesis of the sphingosine analogue involving an oxa Cope rearrangement for the construction of the trans double bond by R. R.prompted us to present our highly stereoselective syntheses of D-erythro-sphingosine and ceramide, using a regio-and stereoselective allylic alkylation reaction[*]. ] that the reaction of an allylic carboxylate with a Grignard reagent in the presence of a catalytic amount of CuCN gave exclusively a y-cross-coupled product. In addition, the reaction of allylic mesylates with PrCu(CN)LiBF3 was also reported['O] to give exclusively y-cross-coupled products with high stereoselectivity. To construct the trans double bond with concomitant chain elongation, an allylic alkylation of the allylic mesylate of retron 3 (Scheme 1) catalyzed by CuCN was envisioned for our sphingosine synthesis. In their syntheses of non-natural L-evythvo-and D-threo-sphingosine, S. Takano et al. described an S N~' replacement of a mesylate by a Grignard reagent catalyzed by CuIL' l].D-xylose was protected as 1,2-O-isopropylidene-~-xylose (4) according to the Moravcova method [12] and transformed via 5 into the known 3,5-dib...

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Synthesis of D-erythro-1-deoxydihydroceramide-1-sulfonic acid

Cited by 15 publications

References 13 publications

Chemistry and biology of the aminosulfonate cysteinolic acid: discovery, distribution, synthesis and metabolism

Chemistry and biology of the aminosulfonate cysteinolic acid: discovery, distribution, synthesis and metabolism

Bacillariophyceae (Diatoms)

A Facile Stereoselective Synthesis of Sphingosine and Ceramide

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