Practical multigram-scale synthesis of 4,6- and 4,8-sphingadienes, chemopreventive sphingoid bases

Chemistry and Physics of Lipids

Volumn 165, Issue 7, 2012, Pages 794-801

  Byun, Hoe Sup ^a   Bittman, Robert ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

Lipid synthesis; Sphingadienine; Sphingoid base; Sphingolipid

Indexed keywords

4,6 SPHINGADIENE; 4,8 SPHINGADIENE; 5 [UNDECADIENYL] 4 (HYDROXYMETHYL) 2 OXAZOLIDINONE; ANTINEOPLASTIC AGENT; N TERT BUTOXYCARBONYL 4 (1' OXO DODECADIENYL) 2,2 DIMETHYL 1,3 OXAZOLIDINE; N TERT BUTOXYCARBONYL 4 (1' OXO HEXADECADIENYL) 2,2 DIMETHYL 1,3 OXAZOLIDINE; OXAZOLIDINE DERIVATIVE; SPHINGOSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL;

ALKADIENES; ANTINEOPLASTIC AGENTS; CYCLIZATION; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SPHINGOLIPIDS; STEREOISOMERISM;

SPHINGOIDEA;

EID: 84868320833     PISSN: 00093084     EISSN: 18732941     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2012.10.002     Document Type: Article

References (38)

1. D.T.U. Abeytunga, J.J. Glick, N.J. Gibson, L.A. Oland, A. Somogyi, V.H. Wysocki, and R. Polt Presence of unsaturated sphingomyelins and changes in their composition during the life cycle of the moth Manduca sexta Journal of Lipid Research 45 2004 1221 1231
2. K. Aida, M. Kinoshita, T. Sugawara, J. Ono, T. Miyazawa, and M. Ohnishi Apoptosis inducement by plant and fungus sphingoid bases in human colon cancer cells Journal of Oleo Science 53 2004 503 510
3. T. Baer, and R.R. Schmidt Glycosyl imidates. synthesis of a cerebroside having a (4E,8E)-sphingadienine moiety from Tetragonia tetragonoides with antiulcerogenic activity Liebigs Annalen der Chemie 1988 669 674
4. E. Barreto-Bergter, G.L. Sassaki, and L.M. de Souza Structural analysis of fungal cerebrosides Frontiers in Microbiology 2 2011 1 11 Article 239
5. R. Bittman Synthetic sphingolipids as bioactive molecules: roles in regulation of cell function Wiley Encyclopedia of Chemical Biology vol. 4 2009 pp. 480-504
6. F.J. Black, and P.J. Kocienski Synthesis of phalluside-1 and Sch II using 1,2-metallate rearrangements Organic and Biomolecular Chemistry 8 2010 1188 1193
7. H.-S. Byun, and R. Bittman Selective deuterium labeling of the sphingoid backbone: facile syntheses of 3,4,5-trideuterio-d-erythro-sphingosine and 3-deuterio-d-erythro-sphingomyelin Chemistry and Physics of Lipids 163 2010 809 813
8. J. Chun, L. He, H.-S. Byun, and R. Bittman Synthesis of ceramide analogs having the C(4)C(5) bond of the long-chain base as part of an aromatic or heteroaromatic system Journal of Organic Chemistry 65 2000 7634 7640
9. 6 ceramides Journal of Organic Chemistry 67 2002 2600 2605
10. 2 inhibitor (-)-cinatrin B Journal of Organic Chemistry 67 2002 4392 4398
11. D. Enders, M. Knopp, and R. Schiffers Asymmetric [3.3]-sigmatropic rearrangements in organic synthesis Tetrahedron: Asymmetry 7 1996 1847 1882
12. H. Fyrst, B. Oskouian, P. Bandhuvula, Y. Gong, H.-S. Byun, R. Bittman, A.R. Lee, and J.D. Saba Natural sphingadienes inhibit Akt-dependent signaling and prevent intestinal tumorigenesis Cancer Research 69 2009 9457 9464
13. H. Fyrst, and J.D. Saba An update on sphingosine-1-phosphate and other sphingolipid mediators Nature Chemical Biology 6 2010 489 497
14. H. Fyrst, X. Zhang, D.R. Herr, H.-S. Byun, R. Bittman, V.H. Phan, G.L. Harris, and J.D. Saba Identification and characterization by electrospray mass spectrometry of endogenous Drosophila sphingadienes Journal of Lipid Research 49 2008 597 600
15. P. Garner, and J.M. Park The synthesis and configurational stability of differentially protected β-hydroxy-α-amino aldehydes Journal of Organic Chemistry 52 1987 2361 2364
16. M. Inamine, M. Suzui, T. Morioka, T. Kinjo, T. Kaneshiro, T. Sugishita, T. Okada, and N. Yoshimi Inhibitory effect of dietary monoglucosylceramide 1-O-beta-glucosyl-N-2′-hydroxyarachidoyl-4,8-sphingadienine on two different categories of colon preneoplastic lesions induced by 1,2-dimethylhydrazine in F344 rats Cancer Science 96 2005 876 881
17. R.E. Ireland, R.H. Mueller, and A.K. Willard The ester enolate Claisen rearrangement. Stereochemical control through selective enolate formation Journal of the American Chemical Society 98 1976 2868 2877
18. K. Itami, K. Terakawa, J.-I. Yoshida, and O. Kajimoto Efficient and rapid CSi bond cleavage in supercritical water Journal of the American Chemical Society 125 2003 6058 6059
19. E. Keinan, and N. Greenspoon Highly chemoselective reductions with polymethylhydrosiloxane and palladium(0) catalyst Journal of Organic Chemistry 48 1983 3545 3548
20. J.-Y. Kim, Y. Mu, X. Jin, S.-H. Park, V.-T. Pham, D.-K. Song, K.-Y. Lee, and W.-H. Ham Efficient and stereoselective synthesis of DAB-1 and d-fagomine via chiral 1,3-oxazine Tetrahedron 67 2011 9426 9432
21. A.M.P. Koskinen, and M.J. Krische γ-Amino-β-keto phosphonates in synthesis: synthesis of the sphingosine skeleton Synlett 1990 665 666
22. A. Kumar, A. Pandurangan, F. Lu, H. Fyrst, M. Zhang, H.-S. Byun, R. Bittman, and J.D. Saba Chemopreventive sphingadienes downregulate Wnt signaling via a PP2A/Akt/GSK3β pathway in colon cancer Carcinogenesis 33 2012 1726 1735
23. S.B. Levery Glycosphingolipid structural analysis and glycosphingolipidomics Methods in Enzymology 405 2005 300 369
24. Z. Liu, Y.-Q. Gong, H.-S. Byun, and R. Bittman An improved two-step synthetic route to primary allylic alcohols from aldehydes New Journal of Chemistry 34 2010 470 475
25. D.V. Lynch, M. Caffrey, J.L. Hogan, and P.L. Steponkus Calorimetric and X-ray diffraction studies of rye glucocerebroside mesomorphism Biophysical Journal 61 1992 1289 1300
26. M. Moreno, C. Murruzzu, and A. Riera Enantioselective synthesis of sphingadienines and aromatic ceramide analogs Organic Letters 13 2011 5184 5187
27. T. Murakami, R. Hirono, and K. Furusawa Efficient stereocontrolled synthesis of sphingadienine derivatives Tetrahedron 61 2005 9233 9241
28. T. Murakami, T. Shimizu, and K. Taguchi Synthesis of sphingadienine-type glucocerebrosides Tetrahedron 56 2000 533 545
29. S.T. Pruett, A. Bushnev, K. Hagedorn, M. Adiga, C.A. Haynes, M.C. Sullards, D.C. Liotta, and A.H. Merrill Jr. Biodiversity of sphingoid bases (sphingosines) and related amino alcohols Journal of Lipid Research 49 2008 1621 1639
30. E. Rozema, M. Binder, M. Bulusu, V. Bochkov, G. Krupitza, and B. Kopp Effects on inflammatory responses by the sphingoid base 4,8-sphingadienine International Journal of Molecular Medicine 30 2012 703 707
31. E. Rozema, R. Popescu, H. Sonderegger, C.W. Huck, J. Winkler, G. Krupitza, E. Urban, and B. Kopp Characterization of glucocerebrosides and the active metabolite 4,8-sphingadienine from Arisaema amurense and Pinellia ternata by NMR and CD spectroscopy and ESI-MS/CID/MS Journal of Agricultural and Food Chemistry 60 2012 7204 7210
32. A.P. Struckhoff, R. Bittman, M.E. Burow, S. Clejan, S. Eliot, T. Hammond, A.B. Scandurro, Y. Tang, and B.S. Beckman Novel ceramide analogs as potential chemotherapeutic agents in breast cancer Journal of Pharmacology and Experimental Therapeutics 309 2004 523 532
33. T. Sugawara, N. Zaima, A. Yamamoto, S. Sakai, R. Noguchi, and T. Hirata Isolation of sphingoid bases of sea cucumber cerebrosides and their cytotoxicity against human colon cancer cells Bioscience, Biotechnology, and Biochemistry 70 2006 2906 2912
34. M.C. Sullards, D.V. Lynch, A.H. Merrill Jr., and J. Adams Structure determination of soybean and wheat glucosylceramide by tandem mass spectrometry Journal of Mass Spectrometry 35 2000 347 353
35. H. Symolon, E.M. Schmelz, D.L. Dillehay, and A.H. Merrill Jr. Dietary soy sphingolipids suppress tumors and gene expression in 1,2-dimethylhydrazine- treated CF1mice and ApcMin/+ mice Journal of Nutrition 134 2004 1157 1161
36. J. Tan, Z. Dong, and J. Liu New cerebrosides from the basidiomycete Cortinarius tenuipes Lipids 38 2003 81 84
37. G. Triola, G. Fabriás, J. Casas, and A. Llebaria Synthesis of cyclopropene analogues of ceramide and their effect on dihydroceramide desaturase Journal of Organic Chemistry 68 2003 9924 9932
38. N2′-type homoallylic coupling reactions mediated by thioether-stabilized copper reagents Journal of Organic Chemistry 65 2000 8146 8151