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Volumn 15, Issue 4, 2004, Pages 213-219

An NMR method towards the routine chiral determination of natural products

Author keywords

Chiral; Enantiomers; NMR; Racemic; Shift reagent; Stereochemistry

Indexed keywords

CHEMICAL REACTIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 4344699379     PISSN: 09580344     EISSN: None     Source Type: Journal    
DOI: 10.1002/pca.760     Document Type: Article
Times cited : (20)

References (33)
  • 1
    • 0036156422 scopus 로고    scopus 로고
    • Anti-microbial activity profiles of the two enantiomers of limonene and carvone isolated from the oils of Mentha spicata and Anethum sowa
    • Aggarwal KK, Khanuja SPS, Ahmad A, Kumar TRS, Gupta VK, Kumar S. 2002. Anti-microbial activity profiles of the two enantiomers of limonene and carvone isolated from the oils of Mentha spicata and Anethum sowa. Flav Fragr J 17: 59-63.
    • (2002) Flav. Fragr. J. , vol.17 , pp. 59-63
    • Aggarwal, K.K.1    Khanuja, S.P.S.2    Ahmad, A.3    Kumar, T.R.S.4    Gupta, V.K.5    Kumar, S.6
  • 2
    • 0036782116 scopus 로고    scopus 로고
    • Putting chirality to work: The strategy of chiral switches
    • Agranat I, Caner H, Caldwell J. 2002. Putting chirality to work: the strategy of chiral switches. Nat Rev Drug Discov 1: 753-768.
    • (2002) Nat. Rev. Drug Discov. , vol.1 , pp. 753-768
    • Agranat, I.1    Caner, H.2    Caldwell, J.3
  • 3
    • 0031575388 scopus 로고    scopus 로고
    • Effect of β-cyclodextrin acetylation on the resolution of phenethylamines with capillary electrophoresis and nuclear magnetic resonance spectroscopy
    • Branch SK, Holzgrabe U, Jefferies TM, Mallwitz H, Matchett MW. 1997. Effect of β-cyclodextrin acetylation on the resolution of phenethylamines with capillary electrophoresis and nuclear magnetic resonance spectroscopy. J Chromatogr 758: 277-292.
    • (1997) J. Chromatogr. , vol.758 , pp. 277-292
    • Branch, S.K.1    Holzgrabe, U.2    Jefferies, T.M.3    Mallwitz, H.4    Matchett, M.W.5
  • 4
    • 0007172292 scopus 로고    scopus 로고
    • Lethal and anti-feedant substance from rhizome of Alpinia galanga SW (Zingiberaceae)
    • Dadang, Riyanto S, Ohsawa K. 1998. Lethal and anti-feedant substance from rhizome of Alpinia galanga SW (Zingiberaceae). Nippon Noyaku Gakkaishi 23: 304-307.
    • (1998) Nippon Noyaku Gakkaishi , vol.23 , pp. 304-307
    • Dadang, A.1    Riyanto, S.2    Ohsawa, K.3
  • 5
    • 33947085552 scopus 로고
    • Nuclear magnetic resonance enantiomer reagents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenyl acetate (MTPA) esters
    • Dale JA, Mosher HS. 1973. Nuclear magnetic resonance enantiomer reagents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenyl acetate (MTPA) esters. J Am Chem Soc 95: 512-519.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 512-519
    • Dale, J.A.1    Mosher, H.S.2
  • 6
    • 0033046670 scopus 로고    scopus 로고
    • Transition metal complexes as auxiliary chromophores in chiroptical studies on carbohydrates
    • Frelek J, Geiger M, Voelter W. 1999. Transition metal complexes as auxiliary chromophores in chiroptical studies on carbohydrates. Curr Org Chem 3: 117-146.
    • (1999) Curr. Org. Chem. , vol.3 , pp. 117-146
    • Frelek, J.1    Geiger, M.2    Voelter, W.3
  • 7
    • 0028892478 scopus 로고
    • Determination of the optical purity of timolol maleate by proton nuclear magnetic resonance spectroscopy with a chiral Pr(III) shift reagent
    • Hanna GM, Lau-Cam CA. 1995. Determination of the optical purity of timolol maleate by proton nuclear magnetic resonance spectroscopy with a chiral Pr(III) shift reagent. J Pharm Biomed Anal 13: 1313-1319.
    • (1995) J. Pharm. Biomed. Anal. , vol.13 , pp. 1313-1319
    • Hanna, G.M.1    Lau-Cam, C.A.2
  • 8
    • 0030965831 scopus 로고    scopus 로고
    • Chiral discrimination by NMR spectroscopy of ephedrine and N-methylephedrine induced by β-cyclodextrin, heptakis(2,3-di-O-acetyl) β-cyclodextrin, and heptakis(6-O-acetyl) β-cyclodextrin
    • Holzgrabe U, Mallwitz H, Branch SK, Jefferies TM, Wiese M. 1997. Chiral discrimination by NMR spectroscopy of ephedrine and N-methylephedrine induced by β-cyclodextrin, heptakis(2,3-di-O-acetyl) β-cyclodextrin, and heptakis(6-O-acetyl) β-cyclodextrin. Chirality 9: 211-219.
    • (1997) Chirality , vol.9 , pp. 211-219
    • Holzgrabe, U.1    Mallwitz, H.2    Branch, S.K.3    Jefferies, T.M.4    Wiese, M.5
  • 9
    • 0000997785 scopus 로고    scopus 로고
    • Samarium(III)-propylenediaminetetraacetate complex: A water-soluble chiral shift reagent for use in high-field NMR
    • Inamoto A, Ogasawara K, Omata K, Kabuto K, Sasaki Y. 2000. Samarium(III)-propylenediaminetetraacetate complex: A water-soluble chiral shift reagent for use in high-field NMR. Org Lett 2: 3543-3545.
    • (2000) Org. Lett. , vol.2 , pp. 3543-3545
    • Inamoto, A.1    Ogasawara, K.2    Omata, K.3    Kabuto, K.4    Sasaki, Y.5
  • 10
    • 0022384294 scopus 로고
    • Acetoxychavicol acetate, an anti-fungal component of Alpinia galanga
    • Janssen AM, Scheffer JJ. 1985. Acetoxychavicol acetate, an anti-fungal component of Alpinia galanga. Planta Med: 51:507-511.
    • (1985) Planta. Med. , vol.51 , pp. 507-511
    • Janssen, A.M.1    Scheffer, J.J.2
  • 11
    • 0001174586 scopus 로고
    • 1′-Acetoxychavicol acetate as a potent inhibitor of tumour promoter-induced Epstein-Barr virus activation from Languas galanga, a traditional Thai condiment
    • Kondo A, Ohigashi H, Murakami A, Suratwadee J, Koshimizu K. 1993. 1′-Acetoxychavicol acetate as a potent inhibitor of tumour promoter-induced Epstein-Barr virus activation from Languas galanga, a traditional Thai condiment. Biosci Biotechnol Biochem 57: 1344-1345.
    • (1993) Biosci. Biotechnol. Biochem. , vol.57 , pp. 1344-1345
    • Kondo, A.1    Ohigashi, H.2    Murakami, A.3    Suratwadee, J.4    Koshimizu, K.5
  • 12
    • 0025790925 scopus 로고
    • Elucidation of the absolute configuration of amino acids and amines by the modified Mosher's method
    • Kusumi T, Fukushima T, Ohtani I, Kakisawa J. 1991. Elucidation of the absolute configuration of amino acids and amines by the modified Mosher's method. Tetrahedron Lett 32: 2939-2942.
    • (1991) Tetrahedron. Lett. , vol.32 , pp. 2939-2942
    • Kusumi, T.1    Fukushima, T.2    Ohtani, I.3    Kakisawa, J.4
  • 13
    • 0017181290 scopus 로고
    • Constituents from seeds of Alpinia galanga Wild. and their anti-ulcer activities
    • Mitsui S, Kobayashi S, Nagahori H, Ogiso A. 1976. Constituents from seeds of Alpinia galanga Wild. and their anti-ulcer activities. Chem Pharm Bull 24: 2377-2382.
    • (1976) Chem. Pharm. Bull. , vol.24 , pp. 2377-2382
    • Mitsui, S.1    Kobayashi, S.2    Nagahori, H.3    Ogiso, A.4
  • 14
    • 0034523991 scopus 로고    scopus 로고
    • Apoptosis induced by 1′-acetoxychavicol acetate in Ehrlich ascites tumour cells is associated with modulation of polyamine metabolism and caspase-3 activation
    • Moffatt J, Hashimoto M, Kojima A, Kennedy DO, Murakami A, Koshimizu K, Ohigashi H, Matsui-Yuasa I. 2000. Apoptosis induced by 1′-acetoxychavicol acetate in Ehrlich ascites tumour cells is associated with modulation of polyamine metabolism and caspase-3 activation. Carcinogenesis 21: 2151-2157.
    • (2000) Carcinogenesis , vol.21 , pp. 2151-2157
    • Moffatt, J.1    Hashimoto, M.2    Kojima, A.3    Kennedy, D.O.4    Murakami, A.5    Koshimizu, K.6    Ohigashi, H.7    Matsui-Yuasa, I.8
  • 15
    • 18244393805 scopus 로고    scopus 로고
    • Involvement of protein tyrosine phosphorylation and reduction of cellular sulphydryl groups in cell death induced by 1′-acetoxychavicol acetate in Ehrlich ascites tumour cells
    • Moffatt J, Kennedy DO, Kojima A, Hasuma T, Yano Y, Otani S, Murakami A, Koshimizu K, Ohigashi H, Matsui-Yuasa I. 2002. Involvement of protein tyrosine phosphorylation and reduction of cellular sulphydryl groups in cell death induced by 1′-acetoxychavicol acetate in Ehrlich ascites tumour cells. Chem Biol Interact 139: 215-230.
    • (2002) Chem. Biol. Interact. , vol.139 , pp. 215-230
    • Moffatt, J.1    Kennedy, D.O.2    Kojima, A.3    Hasuma, T.4    Yano, Y.5    Otani, S.6    Murakami, A.7    Koshimizu, K.8    Ohigashi, H.9    Matsui-Yuasa, I.10
  • 17
    • 0034070594 scopus 로고    scopus 로고
    • Structure-activity relationships of (1′S)- 1′-acetoxychavicol acetate, a major constituent of a Southeast Asian condiment plant Languas galanga, on the inhibition of tumour-promoter-induced Epstein-Barr virus activation
    • Murakami A, Toyota K, Ohura S, Koshimizu K, Ohigashi H. 2000. Structure-activity relationships of (1′S)- 1′-acetoxychavicol acetate, a major constituent of a Southeast Asian condiment plant Languas galanga, on the inhibition of tumour-promoter-induced Epstein-Barr virus activation. J Agric Food Chem 48: 1518-1523.
    • (2000) J. Agric. Food Chem. , vol.48 , pp. 1518-1523
    • Murakami, A.1    Toyota, K.2    Ohura, S.3    Koshimizu, K.4    Ohigashi, H.5
  • 19
    • 2142858450 scopus 로고
    • High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids
    • Ohtani I, Kusumi T, Kashman Y, Kakisawa J. 1991. High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids. J Am Chem Soc 113: 4902-4906.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4902-4906
    • Ohtani, I.1    Kusumi, T.2    Kashman, Y.3    Kakisawa, J.4
  • 20
    • 0035146874 scopus 로고    scopus 로고
    • qNMR - A versatile concept for the validation of natural product reference compounds
    • Pauli GF. 2001. qNMR - a versatile concept for the validation of natural product reference compounds. Phytochem Anal 12: 28-42.
    • (2001) Phytochem. Anal. , vol.12 , pp. 28-42
    • Pauli, G.F.1
  • 21
    • 0031083250 scopus 로고    scopus 로고
    • Chiral recognition detected by fast atom bombardment mass spectrometry
    • Sawada M. 1997. Chiral recognition detected by fast atom bombardment mass spectrometry. Mass Spectrom Rev 16:73-90.
    • (1997) Mass. Spectrom. Rev. , vol.16 , pp. 73-90
    • Sawada, M.1
  • 22
    • 0000810155 scopus 로고    scopus 로고
    • Absolute configuration of 1,n-diols by NMR: The importance of the combined anisotropic effects in bis-arylmethoxyacetates
    • Seco JM, Martino M, Quinoa E, Riguera R. 2000a. Absolute configuration of 1,n-diols by NMR: the importance of the combined anisotropic effects in bis-arylmethoxyacetates. Org Lett2: 3261-3264.
    • (2000) Org. Lett. , vol.2 , pp. 3261-3264
    • Seco, J.M.1    Martino, M.2    Quinoa, E.3    Riguera, R.4
  • 23
    • 0343517106 scopus 로고    scopus 로고
    • The assignment of absolute configurations by NMR of arylmethoxyacetate derivatives: Is this methodology being correctly used? Tetrahedron Asymm
    • Seco JM, Quinoa E, Riguera R. 2000b. The assignment of absolute configurations by NMR of arylmethoxyacetate derivatives: is this methodology being correctly used? Tetrahedron Asymm 11: 2781-2791.
    • (2000) , vol.11 , pp. 2781-2791
    • Seco, J.M.1    Quinoa, E.2    Riguera, R.3
  • 24
    • 0034784296 scopus 로고    scopus 로고
    • Combinatorial evaluation of the chiral discrimination of permethylated carbohydrates using fast-atom bombardment mass spectrometry
    • Shizuma M, Adachi H, Takai Y, Hayashi M, Tanaka J, Takeda T, Sawada M. 2001. Combinatorial evaluation of the chiral discrimination of permethylated carbohydrates using fast-atom bombardment mass spectrometry. Carbohydr Res 335: 275-281.
    • (2001) Carbohydr. Res. , vol.335 , pp. 275-281
    • Shizuma, M.1    Adachi, H.2    Takai, Y.3    Hayashi, M.4    Tanaka, J.5    Takeda, T.6    Sawada, M.7
  • 25
    • 0002341111 scopus 로고    scopus 로고
    • Chiral pharmaceuticals
    • Stinson SC. 2001. Chiral pharmaceuticals. Chem Eng News 79:79-84.
    • (2001) Chem. Eng. News , vol.79 , pp. 79-84
    • Stinson, S.C.1
  • 26
    • 0036741302 scopus 로고    scopus 로고
    • New chemical constituents of Euphorbia quinquecostata and absolute configuration assignment by a convenient Mosher ester procedure carried out in NMR tubes
    • Su BN, Park EJ, Mbwambo ZH, Santarsiero BD, Mesecar AD, Fong HH, Pezzuto JM, Kinghorn AD. 2002. New chemical constituents of Euphorbia quinquecostata and absolute configuration assignment by a convenient Mosher ester procedure carried out in NMR tubes, J Nat Prod 65: 1278-1282.
    • (2002) J. Nat. Prod. , vol.65 , pp. 1278-1282
    • Su, B.N.1    Park, E.J.2    Mbwambo, Z.H.3    Santarsiero, B.D.4    Mesecar, A.D.5    Fong, H.H.6    Pezzuto, J.M.7    Kinghorn, A.D.8
  • 27
    • 33947086629 scopus 로고
    • Correlation of configuration and fluorine-19 chemical shifts of α-methoxy-α-trifluoromethylphenyl acetate
    • Sullivan GR, Dale JA, Mosher HS. 1973. Correlation of configuration and fluorine-19 chemical shifts of α-methoxy-α-trifluoromethylphenyl acetate. J Org Chem 38:2143-2147.
    • (1973) J. Org. Chem. , vol.38 , pp. 2143-2147
    • Sullivan, G.R.1    Dale, J.A.2    Mosher, H.S.3
  • 29
    • 0032346671 scopus 로고    scopus 로고
    • Utilising NMR spectroscopy for assessing drug enantiomeric composition
    • Thunhorst M, Holzgrabe U. 1998. Utilising NMR spectroscopy for assessing drug enantiomeric composition. Magn Reson Chem 36: 211-216.
    • (1998) Magn. Reson. Chem. , vol.36 , pp. 211-216
    • Thunhorst, M.1    Holzgrabe, U.2
  • 31
    • 0001429064 scopus 로고
    • Tris[<3-tertbutylhydrxymethylene>-D-camphorato]europium(III). A reagent for determining enantiomeric purity
    • Whitesides GM, Lewis DW. 1970. Tris[<3-tertbutylhydrxymethylene>-D-camphorato]europium(III). A reagent for determining enantiomeric purity. J Am Chem Soc 92: 6979.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 6979
    • Whitesides, G.M.1    Lewis, D.W.2
  • 33
    • 0028144275 scopus 로고
    • 1H-NMR spectroscopy in the presence of a chiral dirhodium complex
    • 1H-NMR spectroscopy in the presence of a chiral dirhodium complex. Tetrahedron Assymm 5: 27-30.
    • (1994) Tetrahedron. Assymm. , vol.5 , pp. 27-30
    • Wypchlo, K.1    Duddeck, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.