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Volumn 121, Issue 34, 1999, Pages 7773-7777

5-F(2t)-isoprostane, a human hormone?

Author keywords

[No Author keywords available]

Indexed keywords

HORMONE; ISOPROSTANE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

EID: 0033198636     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990859k     Document Type: Article
Times cited : (32)

References (43)
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    • (a) For a summary of isoprostane nomenclature, see Taber, D. F.; Morrow, J. D.; Roberts, L. J., II. Prostaglandins 1997, 53, 63. (b) For an alternative nomenclature system for the isoprostanes, see Rokach, J.; Khanapure, S. P.; Hwang, S. W.; Adiyaman, M.; Lawson, J. A.; FitzGerald, G. A. Prostaglandins 1997, 54, 853.
    • (1997) Prostaglandins , vol.53 , pp. 63
    • Taber, D.F.1    Morrow, J.D.2    Roberts L.J. II3
  • 3
    • 0031418335 scopus 로고    scopus 로고
    • (a) For a summary of isoprostane nomenclature, see Taber, D. F.; Morrow, J. D.; Roberts, L. J., II. Prostaglandins 1997, 53, 63. (b) For an alternative nomenclature system for the isoprostanes, see Rokach, J.; Khanapure, S. P.; Hwang, S. W.; Adiyaman, M.; Lawson, J. A.; FitzGerald, G. A. Prostaglandins 1997, 54, 853.
    • (1997) Prostaglandins , vol.54 , pp. 853
    • Rokach, J.1    Khanapure, S.P.2    Hwang, S.W.3    Adiyaman, M.4    Lawson, J.A.5    FitzGerald, G.A.6
  • 6
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    • 2t-isoprostane: (a) Corey, E. J.; Shih, C.; Shih, N.-Y.; Shimoji, K. Tetrahedron Lett. 1984, 25, 5013. (b) Hwang, S. W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829. (c) Taber, D. F.; Herr, R. J.; Gleave, D. M. J. Org. Chem. 1997, 62, 194. (d) Taber, D. F.; Kanai, K. Tetrahedron 1998, 54, 11767.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 5013
    • Corey, E.J.1    Shih, C.2    Shih, N.-Y.3    Shimoji, K.4
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    • 2t-isoprostane: (a) Corey, E. J.; Shih, C.; Shih, N.-Y.; Shimoji, K. Tetrahedron Lett. 1984, 25, 5013. (b) Hwang, S. W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829. (c) Taber, D. F.; Herr, R. J.; Gleave, D. M. J. Org. Chem. 1997, 62, 194. (d) Taber, D. F.; Kanai, K. Tetrahedron 1998, 54, 11767.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 10829
    • Hwang, S.W.1    Adiyaman, M.2    Khanapure, S.3    Schio, L.4    Rokach, J.5
  • 8
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    • 2t-isoprostane: (a) Corey, E. J.; Shih, C.; Shih, N.-Y.; Shimoji, K. Tetrahedron Lett. 1984, 25, 5013. (b) Hwang, S. W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829. (c) Taber, D. F.; Herr, R. J.; Gleave, D. M. J. Org. Chem. 1997, 62, 194. (d) Taber, D. F.; Kanai, K. Tetrahedron 1998, 54, 11767.
    • (1997) J. Org. Chem. , vol.62 , pp. 194
    • Taber, D.F.1    Herr, R.J.2    Gleave, D.M.3
  • 9
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    • 2t-isoprostane: (a) Corey, E. J.; Shih, C.; Shih, N.-Y.; Shimoji, K. Tetrahedron Lett. 1984, 25, 5013. (b) Hwang, S. W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829. (c) Taber, D. F.; Herr, R. J.; Gleave, D. M. J. Org. Chem. 1997, 62, 194. (d) Taber, D. F.; Kanai, K. Tetrahedron 1998, 54, 11767.
    • (1998) Tetrahedron , vol.54 , pp. 11767
    • Taber, D.F.1    Kanai, K.2
  • 10
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    • 2c-isoprostane: (a) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815. (b) Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. (c) Hwang, S. W.; Adiyaman, M.; Khanapure, S. P.; Rokach, J. Tetrahedron Lett, 1996, 37, 779.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7815
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    • 2c-isoprostane: (a) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815. (b) Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. (c) Hwang, S. W.; Adiyaman, M.; Khanapure, S. P.; Rokach, J. Tetrahedron Lett, 1996, 37, 779.
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    • Vionnet, J.-P.1    Renaud, P.2
  • 12
    • 0030070784 scopus 로고    scopus 로고
    • 2c-isoprostane: (a) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815. (b) Vionnet, J.-P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781. (c) Hwang, S. W.; Adiyaman, M.; Khanapure, S. P.; Rokach, J. Tetrahedron Lett, 1996, 37, 779.
    • (1996) Tetrahedron Lett , vol.37 , pp. 779
    • Hwang, S.W.1    Adiyaman, M.2    Khanapure, S.P.3    Rokach, J.4
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    • See also ref 5d.
    • 2t-isoprostane: Taber, D. F.; Hoerrner, R. S. J. Org. Chem. 1992, 57, 441. (b) See also ref 5d.
  • 27
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    • Ethyl 5-oxopentanoate was prepared by ethanolysis of δ-valerolactone followed by PCC oxidation. For full characterization, see Penn, J. H.; Liu, F. J. Org. Chem. 1994, 59, 2608.
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    • For a complementary approach to the methyl esters of 19 and 10, see Pohnert, G.; Boland, W. Tetrahedron 1996, 52, 10073.
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    • and references therein
    • 13C chemical shifts of allylic methylenes, see Taber, D. F.; You, K. J. Org. Chem. 1995, 60, 139 and references therein.
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    • Taber, D.F.1    You, K.2
  • 30
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    • note
    • 4, the unstable tetraene resulting from β-hydride elimination was the major product.
  • 42
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    • note
    • The ee's were determined by HPLC analyses with a CHIRALCEL OD column (Daicel Chemical Industries Ltd.): detector, UV (254 nm); flow rate, 1 mL/min; mobile phase, hexane/2-PrOH = 95/5 for 45 and 45b, hexane/2-PrOH = 99/1 for 48 and 48a.


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