메뉴 건너뛰기




Volumn 69, Issue 15, 2008, Pages 2737-2742

Determination of the absolute configuration of the glucosinolate methyl sulfoxide group reveals a stereospecific biosynthesis of the side chain

Author keywords

4 Methylsulfinylbutylglucosinolate; Absolute configuration; Arabidopsis thaliana; Epimeric purity; Flavin monooxygenase; Glucoraphanin; Glucosinolate; Nuclear magnetic resonance; Sulforaphane; Sulfoxide

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; GLUCOSINOLATE; MIXED FUNCTION OXIDASE; SULFOXIDE;

EID: 55049121677     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2008.09.008     Document Type: Article
Times cited : (26)

References (24)
  • 1
    • 22244436586 scopus 로고    scopus 로고
    • Role of sulfur chirality in the chemical processes of biology
    • Bentley R. Role of sulfur chirality in the chemical processes of biology. Chem. Soc. Rev. 34 (2005) 609-624
    • (2005) Chem. Soc. Rev. , vol.34 , pp. 609-624
    • Bentley, R.1
  • 2
    • 44549088533 scopus 로고    scopus 로고
    • The methionine sulfoxide reductases: catalysis and substrate specificities
    • Boschi-Muller S., Gand A., and Branlat G. The methionine sulfoxide reductases: catalysis and substrate specificities. Arch. Biochem. Biophys. 474 (2008) 266-273
    • (2008) Arch. Biochem. Biophys. , vol.474 , pp. 266-273
    • Boschi-Muller, S.1    Gand, A.2    Branlat, G.3
  • 3
    • 0037311116 scopus 로고    scopus 로고
    • Variation of glucosinolate accumulation among different organs and developmental stages of Arabidopsis thaliana
    • Brown P., Tokuhisa J., Reichelt M., and Gershenzon J. Variation of glucosinolate accumulation among different organs and developmental stages of Arabidopsis thaliana. Phytochemistry 62 (2003) 471-481
    • (2003) Phytochemistry , vol.62 , pp. 471-481
    • Brown, P.1    Tokuhisa, J.2    Reichelt, M.3    Gershenzon, J.4
  • 4
    • 0345903394 scopus 로고
    • An X-ray crystallographic structural study of sulfoxides derived from 2-phenyl-1,3-dithiane
    • Carey F., Smith P., Maher R., and Bryan R. An X-ray crystallographic structural study of sulfoxides derived from 2-phenyl-1,3-dithiane. J. Org. Chem. 42 (1976) 961-967
    • (1976) J. Org. Chem. , vol.42 , pp. 961-967
    • Carey, F.1    Smith, P.2    Maher, R.3    Bryan, R.4
  • 5
    • 33846198346 scopus 로고
    • The absolute configuration of sulphoxide mustard oils
    • Cheung K., Kjær A., and Sim G. The absolute configuration of sulphoxide mustard oils. Chem. Commun. 6 (1965) 100-102
    • (1965) Chem. Commun. , vol.6 , pp. 100-102
    • Cheung, K.1    Kjær, A.2    Sim, G.3
  • 6
    • 0032584297 scopus 로고    scopus 로고
    • Specificity of alcohol dehydrogenases for sulfoxides
    • Cho H., and Plapp B. Specificity of alcohol dehydrogenases for sulfoxides. Biochemistry 37 (1998) 4482-4489
    • (1998) Biochemistry , vol.37 , pp. 4482-4489
    • Cho, H.1    Plapp, B.2
  • 7
    • 33746155686 scopus 로고    scopus 로고
    • Recent progress in application of spectroscopic methods for assigning absolute configuration of optically active sulfoxides
    • Donnoli M., Superchi S., and Rosini C. Recent progress in application of spectroscopic methods for assigning absolute configuration of optically active sulfoxides. Minireviews Org. Chem. 3 (2006) 77-92
    • (2006) Minireviews Org. Chem. , vol.3 , pp. 77-92
    • Donnoli, M.1    Superchi, S.2    Rosini, C.3
  • 8
    • 0035808553 scopus 로고    scopus 로고
    • The chemical diversity and distribution of glucosinolates and isothiocyanates among plants
    • Fahey J., Zalcmann A., and Talalay P. The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry 56 (2001) 5-51
    • (2001) Phytochemistry , vol.56 , pp. 5-51
    • Fahey, J.1    Zalcmann, A.2    Talalay, P.3
  • 9
    • 34248547027 scopus 로고    scopus 로고
    • Sulforaphane as a promising molecule for fighting cancer
    • Fimognari C., and Hrelia P. Sulforaphane as a promising molecule for fighting cancer. Mutation Res. 635 (2007) 90-104
    • (2007) Mutation Res. , vol.635 , pp. 90-104
    • Fimognari, C.1    Hrelia, P.2
  • 10
    • 0000881454 scopus 로고
    • Vacuolar location of glucosinolates in horseradish root cells
    • Grob K., and Matile P. Vacuolar location of glucosinolates in horseradish root cells. Plant Sci. Lett. 14 (1979) 327-335
    • (1979) Plant Sci. Lett. , vol.14 , pp. 327-335
    • Grob, K.1    Matile, P.2
  • 11
    • 33745218882 scopus 로고    scopus 로고
    • Biology and biochemistry of glucosinolates
    • Halkier B., and Gershenzon J. Biology and biochemistry of glucosinolates. Ann. Rev. Plant Biol. 57 (2006) 303-333
    • (2006) Ann. Rev. Plant Biol. , vol.57 , pp. 303-333
    • Halkier, B.1    Gershenzon, J.2
  • 12
    • 34249783437 scopus 로고    scopus 로고
    • Identification of a flavin-monooxygenase as the S-oxygenating enzyme in aliphatic glucosinolate biosynthesis in Arabidopsis
    • Hansen B., Kliebenstein D., and Halkier B. Identification of a flavin-monooxygenase as the S-oxygenating enzyme in aliphatic glucosinolate biosynthesis in Arabidopsis. Plant J. 50 (2007) 902-910
    • (2007) Plant J. , vol.50 , pp. 902-910
    • Hansen, B.1    Kliebenstein, D.2    Halkier, B.3
  • 13
    • 84987013734 scopus 로고
    • Localization of newly synthesized indole-3-methylglucosinolate (=glucobrassicin) in vacuoles from horseradish (Armoracia rusticana)
    • Helmlinger J., Rausch T., and Hilgenberg W. Localization of newly synthesized indole-3-methylglucosinolate (=glucobrassicin) in vacuoles from horseradish (Armoracia rusticana). Physiol. Plantarum 58 (1983) 302-310
    • (1983) Physiol. Plantarum , vol.58 , pp. 302-310
    • Helmlinger, J.1    Rausch, T.2    Hilgenberg, W.3
  • 14
    • 0033526014 scopus 로고    scopus 로고
    • Formation of glucoraphanin by chemoselective oxidation of natural glucoerucin: a chemoenzymatic route to sulforaphane
    • Iori R., Bernardi R., Gueyrard D., Rollin P., and Palmieri S. Formation of glucoraphanin by chemoselective oxidation of natural glucoerucin: a chemoenzymatic route to sulforaphane. Bioorg. Med. Chem. Lett. 9 (1999) 1047-1048
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 1047-1048
    • Iori, R.1    Bernardi, R.2    Gueyrard, D.3    Rollin, P.4    Palmieri, S.5
  • 15
    • 37049110852 scopus 로고
    • S/αR,SR)-1-(p-bromophenyl)ethyI t-butyl sulphoxide and conformational analysis of diastereoisomeric pairs of 1-phenylethyl t-butyl sulphoxides
    • S/αR,SR)-1-(p-bromophenyl)ethyI t-butyl sulphoxide and conformational analysis of diastereoisomeric pairs of 1-phenylethyl t-butyl sulphoxides. J. Chem. Soc.-Perkin Trans. 2 13 (1976) 1490-1495
    • (1976) J. Chem. Soc.-Perkin Trans. 2 , vol.13 , pp. 1490-1495
    • Kodama, Y.1    Nishihata, K.2    Nishio, M.3
  • 16
    • 85065203081 scopus 로고
    • O-Mesitylenesulfonylhydroxylamine
    • Krause J. O-Mesitylenesulfonylhydroxylamine. Synthesis 3 (1972) 140
    • (1972) Synthesis , vol.3 , pp. 140
    • Krause, J.1
  • 17
    • 33750595994 scopus 로고    scopus 로고
    • The modified Mosheŕs method and the sulfoximine method
    • Kusumi T., Ooi T., Ohkubo Y., and Yabuuchi T. The modified Mosheŕs method and the sulfoximine method. B. Chem. Soc. Jpn. 79 (2006) 965-980
    • (2006) B. Chem. Soc. Jpn. , vol.79 , pp. 965-980
    • Kusumi, T.1    Ooi, T.2    Ohkubo, Y.3    Yabuuchi, T.4
  • 18
    • 1642443170 scopus 로고    scopus 로고
    • Probing the stereochemistry of the active site of gamma-glutamyl transpeptidase using sulfur derivatives of L-glutamic acid
    • Lherbet C., and Keillor J. Probing the stereochemistry of the active site of gamma-glutamyl transpeptidase using sulfur derivatives of L-glutamic acid. Org. Biomol. Chem. 2 (2004) 238-245
    • (2004) Org. Biomol. Chem. , vol.2 , pp. 238-245
    • Lherbet, C.1    Keillor, J.2
  • 19
    • 0001660594 scopus 로고
    • Optical rotatory dispersion and absolute configuration of dialkyl sulfoxides
    • Mislow K., Greenz M., Laur P., and Chisholmz D. Optical rotatory dispersion and absolute configuration of dialkyl sulfoxides. J. Am. Chem. Soc. 87 (1964) 665-666
    • (1964) J. Am. Chem. Soc. , vol.87 , pp. 665-666
    • Mislow, K.1    Greenz, M.2    Laur, P.3    Chisholmz, D.4
  • 20
    • 0037313425 scopus 로고    scopus 로고
    • A proton-pump inhibitor expedition: the case histories of omeprazole and esomeprazole
    • Olbe L., Carlsson E., and Lindberg P. A proton-pump inhibitor expedition: the case histories of omeprazole and esomeprazole. Nat. Rev. Drug Discov. 2 (2003) 132-139
    • (2003) Nat. Rev. Drug Discov. , vol.2 , pp. 132-139
    • Olbe, L.1    Carlsson, E.2    Lindberg, P.3
  • 21
    • 33749856059 scopus 로고    scopus 로고
    • Plant methionine sulfoxide reductase A and B multigenic families
    • Rouhier N., Viera dos Santos C., Tarrago L., and Rey P. Plant methionine sulfoxide reductase A and B multigenic families. Photosynth. Res. 89 (2006) 247-262
    • (2006) Photosynth. Res. , vol.89 , pp. 247-262
    • Rouhier, N.1    Viera dos Santos, C.2    Tarrago, L.3    Rey, P.4
  • 22
    • 0000945561 scopus 로고
    • Isolation of sinigrin and glucotropaeolin from cruciferous seeds
    • Thies W. Isolation of sinigrin and glucotropaeolin from cruciferous seeds. FETT Wissenschaft Technologie-Fat Science Technology 90 (1988) 311-314
    • (1988) FETT Wissenschaft Technologie-Fat Science Technology , vol.90 , pp. 311-314
    • Thies, W.1
  • 23
    • 0033579144 scopus 로고    scopus 로고
    • NMR Spectroscopic determination of the absolute configuration of chiral sulfoxides via N-(methoxyphenylacetyl)sulfoximines
    • Yabuuchi T., and Kusumi T. NMR Spectroscopic determination of the absolute configuration of chiral sulfoxides via N-(methoxyphenylacetyl)sulfoximines. J. Am. Chem. Soc. 121 (1999) 10646-10647
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 10646-10647
    • Yabuuchi, T.1    Kusumi, T.2
  • 24
    • 34548445866 scopus 로고    scopus 로고
    • Discovery and development of sulforaphane as a cancer chemopreventive phytochemical
    • Zhang Y., and Tang L. Discovery and development of sulforaphane as a cancer chemopreventive phytochemical. Acta Pharmacol. Sin. 28 (2007) 1343-1354
    • (2007) Acta Pharmacol. Sin. , vol.28 , pp. 1343-1354
    • Zhang, Y.1    Tang, L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.