메뉴 건너뛰기




Volumn 128, Issue 1-2, 2004, Pages 35-56

Total synthesis of isoprostanes: Discovery and quantitation in biological systems

Author keywords

Free radicals; Isoprostanes; Mass spectrometry; Metabolism; Stereoselective syntheses

Indexed keywords

ISOPROSTANE DERIVATIVE;

EID: 0842346375     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2003.09.011     Document Type: Review
Times cited : (41)

References (66)
  • 3
    • 0032563972 scopus 로고    scopus 로고
    • Syntheses and identification of the most abundant urinary type VI isoprostanes
    • Adiyaman M., Lawson J.A., FitzGerald G.A., Rokach J. Syntheses and identification of the most abundant urinary type VI isoprostanes. Tetrahedron Lett. 39:1998a;7039-7042.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7039-7042
    • Adiyaman, M.1    Lawson, J.A.2    Fitzgerald, G.A.3    Rokach, J.4
  • 5
    • 0029670194 scopus 로고    scopus 로고
    • 2α, a novel index of lipid peroxidation in vivo, by immunoaffinity extraction/gas chromatography-mass spectrometry. Basal levels in smokers and nonsmokers
    • 2α, a novel index of lipid peroxidation in vivo, by immunoaffinity extraction/gas chromatography-mass spectrometry. Basal levels in smokers and nonsmokers. Free Radic. Biol. Med. 20:1996;619-624.
    • (1996) Free Radic. Biol. Med. , vol.20 , pp. 619-624
    • Bachi, A.1    Zuccato, E.2    Baraldi, M.3    Fanelli, R.4    Chiabrando, C.5
  • 6
    • 0344902741 scopus 로고
    • A new method for the deoxygenation of secondary alcohols
    • Barton D.H.R., McCombie S.W. A new method for the deoxygenation of secondary alcohols. J. Chem. Soc. Perkin Trans. 1:1975;1574-1585.
    • (1975) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 1574-1585
    • Barton, D.H.R.1    McCombie, S.W.2
  • 7
  • 8
    • 0000020896 scopus 로고
    • Regio- and stereo-selectivity of alkenyl radical ring closure: A theoretical study
    • Beckwith A.L.J., Schiesser C.H. Regio- and stereo-selectivity of alkenyl radical ring closure: a theoretical study. Tetrahedron. 41:1985;3925-3941.
    • (1985) Tetrahedron , vol.41 , pp. 3925-3941
    • Beckwith, A.L.J.1    Schiesser, C.H.2
  • 13
    • 0028209832 scopus 로고
    • 2, a chemical analog of the biosynthetic pathway
    • 2, a chemical analog of the biosynthetic pathway. Tetrahedron Lett. 35:1994;539-542.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 539-542
    • Corey, E.J.1    Wang, Z.2
  • 15
    • 0024381420 scopus 로고
    • 4 metabolites and their corresponding radioactive precursors
    • 4 metabolites and their corresponding radioactive precursors. J. Org. Chem. 54:1989;3635-3640.
    • (1989) J. Org. Chem. , vol.54 , pp. 3635-3640
    • Delorme, D.1    Girard, Y.2    Rokach, J.3
  • 16
    • 0342696029 scopus 로고
    • Preparation and Diels-Alder reaction of (1E)-1,3,-dimethoxybutadiene
    • Dowd P., Weber W. Preparation and Diels-Alder reaction of (1E)-1,3,-dimethoxybutadiene. J. Org. Chem. 47:1982;4774-4777.
    • (1982) J. Org. Chem. , vol.47 , pp. 4774-4777
    • Dowd, P.1    Weber, W.2
  • 17
    • 0037204690 scopus 로고    scopus 로고
    • 2t-isoprostanes by a biomimetic process using the cyclization of acyclic dihydroxylated octa-5,7-dienyl radicals
    • 2t-isoprostanes by a biomimetic process using the cyclization of acyclic dihydroxylated octa-5,7-dienyl radicals. J. Org. Chem. 67:2002;3615-3624.
    • (2002) J. Org. Chem. , vol.67 , pp. 3615-3624
    • Durand, T.1    Guy, A.2    Vidal, J.P.3    Rossi, J.C.4
  • 19
    • 0000553367 scopus 로고
    • [ 4+2 ] cycloaddition of azodicarboxylate and glycols: A novel and simple method for the preparation of 2-amino-2-deoxycarbohydrates
    • Fitzsimmons B.J., Leblanc Y., Rokach J. [. 4+2 ] cycloaddition of azodicarboxylate and glycols: a novel and simple method for the preparation of 2-amino-2-deoxycarbohydrates J. Am. Chem. Soc. 109:1987;285-286.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 285-286
    • Fitzsimmons, B.J.1    Leblanc, Y.2    Rokach, J.3
  • 22
    • 0023657927 scopus 로고
    • Identification of novel arachidonic acid metabolites formed by prostaglandin H synthase
    • Hecker M., Ullrich V., Fischer C., Meese C.O. Identification of novel arachidonic acid metabolites formed by prostaglandin H synthase. Eur. J. Biochem. 169:1987;113-123.
    • (1987) Eur. J. Biochem. , vol.169 , pp. 113-123
    • Hecker, M.1    Ullrich, V.2    Fischer, C.3    Meese, C.O.4
  • 29
    • 0025942580 scopus 로고
    • 2α by the controlled, one-step, palladium-promoted, intramolecular coupling of three different alkenes
    • 2α by the controlled, one-step, palladium-promoted, intramolecular coupling of three different alkenes. J. Am. Chem. Soc. 113:1991;7815-7816.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7815-7816
    • Larock, R.C.1    Lee, N.H.2
  • 31
    • 0033609811 scopus 로고    scopus 로고
    • Isoprostanes: Formation, analysis and use as indices of lipid peroxidation in vivo
    • Lawson J.A., Rokach J., FitzGerald G.A. Isoprostanes: formation, analysis and use as indices of lipid peroxidation in vivo. J. Biol. Chem. 274:1999;24441-24444.
    • (1999) J. Biol. Chem. , vol.274 , pp. 24441-24444
    • Lawson, J.A.1    Rokach, J.2    Fitzgerald, G.A.3
  • 32
    • 0001745139 scopus 로고
    • [ 4+2 ] cycloaddition reaction of dibenzyl azodicarboxylate and glycals
    • Leblanc Y., Fitzsimmons B.J., Springer J.P., Rokach J. [. 4+2 ] cycloaddition reaction of dibenzyl azodicarboxylate and glycals J. Am. Chem. Soc. 111:1989;2995-3000.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 2995-3000
    • Leblanc, Y.1    Fitzsimmons, B.J.2    Springer, J.P.3    Rokach, J.4
  • 35
    • 0026064384 scopus 로고
    • Quantification of noncyclooxygenase derived prostanoids as a marker of oxidative stress
    • Morrow J.D., Roberts L.J. II Quantification of noncyclooxygenase derived prostanoids as a marker of oxidative stress. Free Radic. Biol. Med. 10:1991;195-200.
    • (1991) Free Radic. Biol. Med. , vol.10 , pp. 195-200
    • Morrow, J.D.1    Roberts II, L.J.2
  • 36
    • 0025058849 scopus 로고
    • Noncyclooxygenase oxidative formation of a series of novel prostaglandins: Analytical ramifications for measurement of eicosanoids
    • Morrow J.D., Harris T.M., Roberts L.J. II Noncyclooxygenase oxidative formation of a series of novel prostaglandins: analytical ramifications for measurement of eicosanoids. Anal. Biochem. 184:1990a;1-10.
    • (1990) Anal. Biochem. , vol.184 , pp. 1-10
    • Morrow, J.D.1    Harris, T.M.2    Roberts II, L.J.3
  • 38
    • 84988070764 scopus 로고
    • Asymmetric synthesis of ent-Corey lactone alcohol and its 12-(all-cis)- and 11-epimers via free radical 5-exo-trig-C,C cyclization
    • Mulzer, J., Kermanchahi, A.K., Buschmann, J., Luger, P., 1994. Asymmetric synthesis of ent-Corey lactone alcohol and its 12-(all-cis)- and 11-epimers via free radical 5-exo-trig-C,C cyclization. Liebigs Ann. Chem. 531-539.
    • (1994) Liebigs Ann. Chem. , pp. 531-539
    • Mulzer, J.1    Kermanchahi, A.K.2    Buschmann, J.3    Luger, P.4
  • 39
    • 0345054821 scopus 로고    scopus 로고
    • Metabolism of leukotrienes in vitro and in vivo
    • S.H.a.S.-E. Dahlen (Ed.), Blackwell Science Ltd., London
    • Murphy, R.C., Wheelan, P., 1997. Metabolism of leukotrienes in vitro and in vivo. In: S.H.a.S.-E. Dahlen (Ed.), SRS-A to Leukotrienes: The Dawning of a New Treatment. Blackwell Science Ltd., London, pp. 101-120.
    • (1997) SRS-a to Leukotrienes: The Dawning of a New Treatment , pp. 101-120
    • Murphy, R.C.1    Wheelan, P.2
  • 41
    • 0001160895 scopus 로고
    • Isolation and characterization of bicyclo endoperoxides derived from methyl linolenate
    • O'Connor D.E., Mihelich E.D., Coleman M.C. Isolation and characterization of bicyclo endoperoxides derived from methyl linolenate. J. Am. Chem. Soc. 103:1981;223-224.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 223-224
    • O'Connor, D.E.1    Mihelich, E.D.2    Coleman, M.C.3
  • 42
    • 0021444203 scopus 로고
    • Stereochemical course of the autoxidative cyclization of lipid hydroperoxides to prostaglandin-like bicyclo endoperoxides
    • O'Connor D.E., Mihelich E.D., Coleman M.C. Stereochemical course of the autoxidative cyclization of lipid hydroperoxides to prostaglandin-like bicyclo endoperoxides. J. Am. Chem. Soc. 106:1984;3577-3584.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 3577-3584
    • O'Connor, D.E.1    Mihelich, E.D.2    Coleman, M.C.3
  • 44
    • 0016864008 scopus 로고
    • Peroxy radical cyclization as a model for prostaglandin biosynthesis
    • Porter N.A., Funk M.O. Peroxy radical cyclization as a model for prostaglandin biosynthesis. J. Org. Chem. 40:1975;3614-3615.
    • (1975) J. Org. Chem. , vol.40 , pp. 3614-3615
    • Porter, N.A.1    Funk, M.O.2
  • 50
    • 0037164005 scopus 로고    scopus 로고
    • Preparation of isoprostanes and neuroprostanes
    • Quan L.G., Cha J.K. Preparation of isoprostanes and neuroprostanes. J. Am. Chem. Soc. 124:2002;12424-12425.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 12424-12425
    • Quan, L.G.1    Cha, J.K.2
  • 51
    • 0842342245 scopus 로고
    • Reagent
    • Reagent, 1986. Aldrichim. Acta 19, 42.
    • (1986) Aldrichim. Acta , vol.19 , pp. 42
  • 53
    • 0037189134 scopus 로고    scopus 로고
    • Total synthesis of isoprostanes via the two-component coupling process
    • Rodriguez A.R., Spur B.W. Total synthesis of isoprostanes via the two-component coupling process. Tetrahedron Lett. 43:2002;4575-4579.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 4575-4579
    • Rodriguez, A.R.1    Spur, B.W.2
  • 57
    • 0025572770 scopus 로고
    • 4 elimination and metabolism in normal human subjects
    • 4 elimination and metabolism in normal human subjects. J. Biol. Chem. 265:1990;21771-21778.
    • (1990) J. Biol. Chem. , vol.265 , pp. 21771-21778
    • Sala, A.1    Voelkel, N.2    MacLouf, J.3
  • 63
    • 0028063529 scopus 로고
    • Facile preparation of (±)-12-epiprostaglandins from 7-oxabicyclo[2.2.1]hept-5-en-2-one via an all-cis-formyllactone related to Corey lactone
    • Vionnet J.-P., Renaud P. Facile preparation of (±)-12- epiprostaglandins from 7-oxabicyclo[2.2.1]hept-5-en-2-one via an all-cis-formyllactone related to Corey lactone. Helv. Chim. Acta. 77:1994;1781-1790.
    • (1994) Helv. Chim. Acta , vol.77 , pp. 1781-1790
    • Vionnet, J.-P.1    Renaud, P.2
  • 65
    • 0029937572 scopus 로고    scopus 로고
    • 2- isoprostanes formed by free radical oxidation of arachidonic acid
    • 2-isoprostanes formed by free radical oxidation of arachidonic acid. J. Am. Soc. Mass Spectrom. 7:1996;490-499.
    • (1996) J. Am. Soc. Mass Spectrom. , vol.7 , pp. 490-499
    • Waugh, R.J.1    Murphy, R.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.