Journal ArticleDOI
A short and efficient stereoselective synthesis of all four diastereomers of sphingosine
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In this article, a diastereoselective reduction of the N-trityl protected α′-amino enone derivative 5 with NaBH4 was achieved.Abstract:
Practical syntheses of all four stereomers of sphingosine from serine have been achieved through highly diastereoselective reduction of the N-trityl protected α′-amino enone derivative 5 with NaBH4 and reduction of the free α′-amino enone derivative 7 with Zn(BH4)2.read more
Citations
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Journal ArticleDOI
Characterization of overall ceramide species in human stratum corneum.
Yoshinori Masukawa,Hirofumi Narita,Eri Shimizu,Naoki Kondo,Yoshiya Sugai,Tsuyoshi Oba,Rika Homma,Junko Ishikawa,Yutaka Takagi,Takashi Kitahara,Yoshinori Takema,Katsumi Kita +11 more
TL;DR: Overall CER species in human stratum corneum are characterized and a new CER class consisting of α-hydroxy fatty acid and dihydrosphingosine moieties is discovered, in addition to the 10 classes generally known.
Journal ArticleDOI
Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine.
Elin Abraham,Stephen G. Davies,Nicholas L. Millican,Rebecca L. Nicholson,Paul M. Roberts,Andrew D. Smith +5 more
TL;DR: The highly diastereoselective anti-aminohydroxylation of alpha,beta-unsaturated esters, via conjugate addition of lithium and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine, has been used as the key step in the asymmetric synthesis of N,O,O-diacetyl xestoaminol C.
Journal ArticleDOI
A practical synthesis of D-erythro-sphingosine using a cross-metathesis approach
Staffan Torssell,Peter Somfai +1 more
TL;DR: In this paper, a short and practical synthesis of D-erythro-sphingosine was described, starting from a vinylepoxide and an E-selective cross-metathesis, affording the target molecule in 5 steps and 51% overall yield.
Journal ArticleDOI
An efficient and general enantioselective synthesis of sphingosine, phythosphingosine, and 4-substituted derivatives.
TL;DR: A general and efficient protocol for the enantioselective synthesis of sphingosine, phythosphingoine, and 4-substituted derivatives was established.
References
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Journal ArticleDOI
Functions of Ceramide in Coordinating Cellular Responses to Stress
TL;DR: A spectrum of inducers of ceramide accumulation and the nature of Ceramide-mediated responses suggest that ceramide is a key component of intracellular stress response pathways.
Book
Biochemistry of lipids, lipoproteins, and membranes
Dennis E. Vance,Jean E. Vance +1 more
TL;DR: This chapter discusses the physical properties and functional Roles of Lipids in Membranes, as well as the Dynamics of Lipoprotein Transport in the Circulatory System.
Journal ArticleDOI
The sphingomyelin pathway in tumor necrosis factor and interleukin-1 signaling
Richard Kolesnick,David W. Golde +1 more
TL;DR: Accumulating evidence suggests that the sphingomyelin metabolic pathway is a commonly employed pathway that could be exploited therapeutically by tumor necrosis factor a and interleukin-18 to effect signal transduction by their receptors.
Journal ArticleDOI
Horner-wadsworth-emmons reaction: Use of lithium chloride and an amine for base-sensitive compounds
Mary A. Blanchette,William Choy,Jeffery T. Davis,Amy P. Essenfeld,Satoru Masamune,William R. Roush,Toshiya Sakai +6 more
TL;DR: A mild olefination procedure, utilizing LiCl and an amine, has been developed for use with base-sensitive aldehydes and phosphonates as discussed by the authors.
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A practical synthesis of D-erythro-sphingosine using a cross-metathesis approach
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