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Volumn 4, Issue , 2013, Pages

NMR spectroscopic detection of chirality and enantiopurity in referenced systems without formation of diastereomers

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINO ACID; CARBOXYLIC ACID; ESTER; PORPHYRINOGEN;

EID: 84891809748     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms3188     Document Type: Article
Times cited : (101)

References (54)
  • 2
    • 75749090864 scopus 로고    scopus 로고
    • (eds Jacobsen, E. N., Pfaltz, A. & Yamamoto, H.) Springer
    • Comprehensive organic catalysis, Vols I to III (eds Jacobsen, E. N., Pfaltz, A. & Yamamoto, H.) (Springer, 1999).
    • (1999) Comprehensive Organic Catalysis , vol.1-3
  • 4
    • 0037436454 scopus 로고    scopus 로고
    • Privileged chiral catalysts
    • Yoon, T. P. & Jacobsen, E. N. Privileged chiral catalysts. Science 299, 1691-1693 (2003).
    • (2003) Science , vol.299 , pp. 1691-1693
    • Yoon, T.P.1    Jacobsen, E.N.2
  • 5
    • 0035793664 scopus 로고    scopus 로고
    • Chiral molecular recognition on formation of a metalloanthocyanin: A supramolecular metal complex pigment from blue flowers of Salvia patens
    • Kondo, T., Oyama, K. & Yoshida, K. Chiral molecular recognition on formation of a metalloanthocyanin: a supramolecular metal complex pigment from blue flowers of Salvia patens. Angew. Chem. Int. Ed 40, 894-897 (2001).
    • (2001) Angew. Chem. Int. Ed , vol.40 , pp. 894-897
    • Kondo, T.1    Oyama, K.2    Yoshida, K.3
  • 6
    • 0037065290 scopus 로고    scopus 로고
    • Enantioselective formation of a dynamic hydrogen-bonded assembly based on the chiral memory concept
    • Ishi-i, T., Crego-Calama, M., Timmerman, P., Reinhoudt, D. N. & Shinkai, S. Enantioselective formation of a dynamic hydrogen-bonded assembly based on the chiral memory concept. J. Am. Chem. Soc. 124, 14631-14641 (2002).
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 14631-14641
    • Ishi-i, T.1    Crego-Calama, M.2    Timmerman, P.3    Reinhoudt, D.N.4    Shinkai, S.5
  • 7
    • 1842607368 scopus 로고    scopus 로고
    • Mechanism of helix induction on a stereoregular poly((4-carboxyphenyl) acetylene) with chiral amines and memory of the macromolecular helicity assisted by interaction with achiral amines
    • Maeda, K., Morino, K., Okamoto, Y., Sato, T. & Yashima, E. Mechanism of helix induction on a stereoregular poly((4-carboxyphenyl)acetylene) with chiral amines and memory of the macromolecular helicity assisted by interaction with achiral amines. J. Am. Chem. Soc. 126, 4329-4342 (2004).
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 4329-4342
    • Maeda, K.1    Morino, K.2    Okamoto, Y.3    Sato, T.4    Yashima, E.5
  • 9
    • 45749105171 scopus 로고    scopus 로고
    • Conformationally driven asymmetric induction of a catalytic dendrimer
    • Yu, J., RajanBabu, T. V. & Parquette, J. R. Conformationally driven asymmetric induction of a catalytic dendrimer. J. Am. Chem. Soc. 130, 7845-7847 (2008).
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 7845-7847
    • Yu, J.1    RajanBabu, T.V.2    Parquette, J.R.3
  • 10
    • 0034648801 scopus 로고    scopus 로고
    • Helical self-assembled polymers from cooperative stacking of hydrogen-bonded pairs
    • Hirschberg, J. H. K. K. et al. Helical self-assembled polymers from cooperative stacking of hydrogen-bonded pairs. Nature 407, 167-170 (2000).
    • (2000) Nature , vol.407 , pp. 167-170
    • Hirschberg, J.H.K.K.1
  • 11
    • 0029785123 scopus 로고    scopus 로고
    • Colorimetric chiral recognition by a molecular sensor
    • Kubo, Y., Maeda, S., Tokita, S. & Kubo, M. Colorimetric chiral recognition by a molecular sensor. Nature 382, 522-524 (1996).
    • (1996) Nature , vol.382 , pp. 522-524
    • Kubo, Y.1    Maeda, S.2    Tokita, S.3    Kubo, M.4
  • 12
    • 1642404953 scopus 로고    scopus 로고
    • Facile quantification of enantiomeric excess and concentration with indicator-displacement assays: An example in the analyses of α-hydroxyacids
    • Zhu, L. & Anslyn, E. V. Facile quantification of enantiomeric excess and concentration with indicator-displacement assays: an example in the analyses of α-hydroxyacids. J. Am. Chem. Soc. 126, 3676-3677 (2004).
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 3676-3677
    • Zhu, L.1    Anslyn, E.V.2
  • 13
    • 0000868442 scopus 로고    scopus 로고
    • Visual enantiomeric recognition using chiral phenolphthalein derivatives
    • Tsubaki, K. et al. Visual enantiomeric recognition using chiral phenolphthalein derivatives. Org. Lett. 3, 4071-4073 (2001).
    • (2001) Org. Lett. , vol.3 , pp. 4071-4073
    • Tsubaki, K.1
  • 14
    • 0034616785 scopus 로고    scopus 로고
    • Chirality-memory molecule: Crystallographic and spectroscopic studies on dynamic molecular recognition events by fully substituted chiral porphyrins
    • Mizuno, Y., Aida, T. & Yamaguchi, K. Chirality-memory molecule: crystallographic and spectroscopic studies on dynamic molecular recognition events by fully substituted chiral porphyrins. J. Am. Chem. Soc. 122, 5278-5285 (2000).
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 5278-5285
    • Mizuno, Y.1    Aida, T.2    Yamaguchi, K.3
  • 15
    • 47749111758 scopus 로고    scopus 로고
    • High-throughput screening of identity, enantiomeric excess, and concentration using MLCT transitions in CD spectroscopy
    • Nieto, S., Lynch, V. M., Anslyn, E. V., Kim, H. & Chin, J. High-throughput screening of identity, enantiomeric excess, and concentration using MLCT transitions in CD spectroscopy. J. Am. Chem. Soc. 130, 9232-9233 (2008).
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 9232-9233
    • Nieto, S.1    Lynch, V.M.2    Anslyn, E.V.3    Kim, H.4    Chin, J.5
  • 16
    • 0029272840 scopus 로고
    • Chiral discrimination of monosaccharides using a fluorescent molecular sensor
    • James, T. D., Sandanayake, K. R. A. S. & Shinkai, S. Chiral discrimination of monosaccharides using a fluorescent molecular sensor. Nature 374, 345-347 (1995).
    • (1995) Nature , vol.374 , pp. 345-347
    • James, T.D.1    Sandanayake, K.R.A.S.2    Shinkai, S.3
  • 17
    • 0346093984 scopus 로고    scopus 로고
    • High-throughput screening by using a blue-fluorescent antibody sensor
    • Matsushita, M. et al. High-throughput screening by using a blue-fluorescent antibody sensor. Angew. Chem. Int. Ed 42, 5984-5987 (2003).
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 5984-5987
    • Matsushita, M.1
  • 18
    • 8844238341 scopus 로고    scopus 로고
    • Enantioselective sensing of chiral carboxylic acids
    • Mei, X. & Wolf, C. Enantioselective sensing of chiral carboxylic acids. J. Am. Chem. Soc. 126, 14736-14737 (2004).
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 14736-14737
    • Mei, X.1    Wolf, C.2
  • 19
    • 78650272206 scopus 로고    scopus 로고
    • Pseudoenantiomeric fluorescent sensors in a chiral assay
    • Yu, S. & Pu, L. Pseudoenantiomeric fluorescent sensors in a chiral assay. J. Am. Chem. Soc. 132, 17698-17700 (2010).
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 17698-17700
    • Yu, S.1    Pu, L.2
  • 20
    • 77954303578 scopus 로고    scopus 로고
    • Electrochemical method for the determination of enantiomeric excess of binol using redox-active boronic acids as chiral sensors
    • Mirri, G. et al. Electrochemical method for the determination of enantiomeric excess of binol using redox-active boronic acids as chiral sensors. J. Am. Chem. Soc. 132, 8903-8905 (2010).
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 8903-8905
    • Mirri, G.1
  • 21
    • 33845196263 scopus 로고    scopus 로고
    • Chiral recognition in cucurbituril cavities
    • Rekharsky, M. V. et al. Chiral recognition in cucurbituril cavities. J. Am. Chem. Soc. 128, 14871-14880 (2006).
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 14871-14880
    • Rekharsky, M.V.1
  • 22
    • 0034837951 scopus 로고    scopus 로고
    • Supramolecular chirogenesis in zinc porphyrins: Mechanism, role of guest structure, and application for the absolute configuration determination
    • Borovkov, V. V., Lintuluoto, J. M. & Inoue, Y. Supramolecular chirogenesis in zinc porphyrins: mechanism, role of guest structure, and application for the absolute configuration determination. J. Am. Chem. Soc. 123, 2979-2989 (2001).
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 2979-2989
    • Borovkov, V.V.1    Lintuluoto, J.M.2    Inoue, Y.3
  • 23
    • 0035915377 scopus 로고    scopus 로고
    • Chirality-transfer control using a heterotopic zinc(II) porphyrin dimer
    • Kubo, Y. et al. Chirality-transfer control using a heterotopic zinc(II) porphyrin dimer. J. Am. Chem. Soc. 123, 12700-12701 (2001).
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 12700-12701
    • Kubo, Y.1
  • 24
    • 39049128533 scopus 로고    scopus 로고
    • Fluorinated porphyrin tweezer: A powerful reporter of absolute configuration for erythro and threo diols, amino alcohols, and diamines
    • Li, X., Tanasova, M., Vasileiou, C. & Borhan, B. Fluorinated porphyrin tweezer: a powerful reporter of absolute configuration for erythro and threo diols, amino alcohols, and diamines. J. Am. Chem. Soc. 130, 1885-1893 (2008).
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 1885-1893
    • Li, X.1    Tanasova, M.2    Vasileiou, C.3    Borhan, B.4
  • 25
    • 0037019533 scopus 로고    scopus 로고
    • Absolute configurational assignments of secondary amines by CD-sensitive dimeric zinc porphyrin host
    • Huang, X. et al. Absolute configurational assignments of secondary amines by CD-sensitive dimeric zinc porphyrin host. J. Am. Chem. Soc. 124, 10320-10335 (2002).
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10320-10335
    • Huang, X.1
  • 26
    • 0010640653 scopus 로고
    • α-Methoxy-α-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines
    • Dale, J. A., Dull, D. L. & Mosher, H. S. α-Methoxy-α- trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines. J. Org. Chem. 34, 2543-2549 (1969).
    • (1969) J. Org. Chem. , vol.34 , pp. 2543-2549
    • Dale, J.A.1    Dull, D.L.2    Mosher, H.S.3
  • 27
    • 0000237404 scopus 로고
    • NMR determination of enantiomeric purity
    • Parker, D. NMR determination of enantiomeric purity. Chem. Rev. 91, 1441-1457 (1991).
    • (1991) Chem. Rev. , vol.91 , pp. 1441-1457
    • Parker, D.1
  • 28
    • 79951503684 scopus 로고    scopus 로고
    • Assignment of absolute configuration using chiral reagents and NMR spectroscopy
    • Wenzel, T. J. & Chisholm, C. D. Assignment of absolute configuration using chiral reagents and NMR spectroscopy. Chirality 23, 190-214 (2011).
    • (2011) Chirality , vol.23 , pp. 190-214
    • Wenzel, T.J.1    Chisholm, C.D.2
  • 29
    • 59849105178 scopus 로고    scopus 로고
    • Chiral recognition of ethers by NMR spectroscopy
    • Duddeck, H. & Gó mez, E. D. Chiral recognition of ethers by NMR spectroscopy. Chirality 21, 51-68 (2009).
    • (2009) Chirality , vol.21 , pp. 51-68
    • Duddeck, H.1    Gó Mez, E.D.2
  • 30
    • 0035907736 scopus 로고    scopus 로고
    • 4-structure - Versatile chiral shift agents
    • 4-structure - versatile chiral shift agents. Chem. Eur. J. 7, 2676-2686 (2001).
    • (2001) Chem. Eur. J. , vol.7 , pp. 2676-2686
    • Schwenninge, R.1
  • 31
    • 33947298131 scopus 로고
    • Diastereomeric solute-solute interactions of enantiomers in achiral solvents. Nonequivalence of the nuclear magnetic resonance spectra of racemic and optically active dihydroquinine
    • Williams, T., Pitcher, R. G., Bommer, P., Gutzwiller, J. & Uskokovć, M. Diastereomeric solute-solute interactions of enantiomers in achiral solvents. Nonequivalence of the nuclear magnetic resonance spectra of racemic and optically active dihydroquinine. J. Am. Chem. Soc. 91, 1871-1872 (1969).
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 1871-1872
    • Williams, T.1    Pitcher, R.G.2    Bommer, P.3    Gutzwiller, J.4    Uskokovć, M.5
  • 32
    • 33845373765 scopus 로고
    • Self-induced nonequivalence in the association of D and L-amino acid derivatives
    • Dobashi, A., Saito, N., Motoyama, Y. & Hara, S. Self-induced nonequivalence in the association of D and L-amino acid derivatives. J. Am. Chem. Soc. 108, 307-308 (1986).
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 307-308
    • Dobashi, A.1    Saito, N.2    Motoyama, Y.3    Hara, S.4
  • 33
    • 0000191002 scopus 로고
    • Enantiomeric purity determination of 1,2-diols through NMR spectroscopy without chiral auxiliaries
    • Luchinat, C. & Roelens, S. Enantiomeric purity determination of 1,2-diols through NMR spectroscopy without chiral auxiliaries. J. Am. Chem. Soc. 108, 4873-4878 (1986).
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 4873-4878
    • Luchinat, C.1    Roelens, S.2
  • 34
    • 0000185594 scopus 로고
    • 31P NMR method for the determination of enantiomeric purity of alcohols not requiring chiral auxiliary compounds
    • 31P NMR method for the determination of enantiomeric purity of alcohols not requiring chiral auxiliary compounds. J. Am. Chem. Soc. 107, 4798-4799 (1985).
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 4798-4799
    • Feringa, B.L.1    Smaardijk, A.2    Wynberg, H.3
  • 35
    • 67650495495 scopus 로고    scopus 로고
    • Nuclear magnetic resonance signaling of molecular chiral information using an achiral reagent
    • Shundo, A., Labuta, J., Hill, J. P., Ishihara, S. & Ariga, K. Nuclear magnetic resonance signaling of molecular chiral information using an achiral reagent. J. Am. Chem. Soc. 131, 9494-9495 (2009).
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 9494-9495
    • Shundo, A.1    Labuta, J.2    Hill, J.P.3    Ishihara, S.4    Ariga, K.5
  • 36
    • 79952595399 scopus 로고    scopus 로고
    • Chirality sensing by nonchiral porphines
    • Labuta, J. et al. Chirality sensing by nonchiral porphines. Chem. Eur. J. 17, 3558-3561 (2011).
    • (2011) Chem. Eur. J. , vol.17 , pp. 3558-3561
    • Labuta, J.1
  • 37
    • 0032506946 scopus 로고    scopus 로고
    • Quantitative description of the facial discrimination of molecules containing a prochiral group by NMR in a chiral liquid crystal
    • Merlet, D., Loewenstein, A., Smadja, W., Courtieu, J. & Lesot, P. Quantitative description of the facial discrimination of molecules containing a prochiral group by NMR in a chiral liquid crystal. J. Am. Chem. Soc. 120, 963-969 (1998).
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 963-969
    • Merlet, D.1    Loewenstein, A.2    Smadja, W.3    Courtieu, J.4    Lesot, P.5
  • 38
    • 0000499384 scopus 로고    scopus 로고
    • The relationship between molecular symmetry and second-rank orientational order parameters formolecules in chiral liquid crystalline solvents
    • Merlet, D., Emsley, J. W., Lesot, P. & Courtieu, J. The relationship between molecular symmetry and second-rank orientational order parameters formolecules in chiral liquid crystalline solvents. J. Chem. Phys. 111, 6890-6896 (1999).
    • (1999) J. Chem. Phys. , vol.111 , pp. 6890-6896
    • Merlet, D.1    Emsley, J.W.2    Lesot, P.3    Courtieu, J.4
  • 41
    • 33947332027 scopus 로고
    • Applications of the sequence rule. I. Naming the paired ligands g,g at a tetrahedral atom xggij. II. Naming the two faces of a trigonal atom yghi
    • Hanson, K. R. Applications of the sequence rule. I. Naming the paired ligands g,g at a tetrahedral atom xggij. II. Naming the two faces of a trigonal atom yghi. J. Am. Chem. Soc. 88, 2731-2742 (1966).
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 2731-2742
    • Hanson, K.R.1
  • 42
    • 84870040189 scopus 로고    scopus 로고
    • IUPAC Gold Book: http://goldbook.iupac.org/P04859.html (2012).
    • (2012) IUPAC Gold Book
  • 43
    • 37049087887 scopus 로고
    • 1,2-diphenylethane-1,2-diamine: An effective NMR chiral solvating agent for chiral carboxylic acids
    • Fulwood, R. & Parker, D. 1,2-diphenylethane-1,2-diamine: An effective NMR chiral solvating agent for chiral carboxylic acids. J. Chem. Soc., Perkin Trans. 2 57-64 (1994).
    • (1994) J. Chem. Soc., Perkin Trans. 2 , pp. 57-64
    • Fulwood, R.1    Parker, D.2
  • 44
    • 0002676092 scopus 로고
    • Prostereoisomerism (Prochirality)
    • Eliel, E. L. Prostereoisomerism (Prochirality). Top. Curr. Chem. 105, 1-76 (1982).
    • (1982) Top. Curr. Chem. , vol.105 , pp. 1-76
    • Eliel, E.L.1
  • 45
    • 0009924476 scopus 로고
    • Stereoisomerism and local chirality
    • Mislow, K. & Siege, J. Stereoisomerism and local chirality. J. Am. Chem. Soc. 106, 3319-3328 (1984).
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 3319-3328
    • Mislow, K.1    Siege, J.2
  • 47
    • 84859150644 scopus 로고    scopus 로고
    • Colorimetric detection of trace water in tetrahydrofuran using N,N'-substituted oxoporphyrinogens
    • Ishihara, S. et al. Colorimetric detection of trace water in tetrahydrofuran using N,N'-substituted oxoporphyrinogens. Chem. Commun. 48, 3933-3935 (2012).
    • (2012) Chem. Commun. , vol.48 , pp. 3933-3935
    • Ishihara, S.1
  • 48
    • 0016563662 scopus 로고
    • On the application of Job's method of continuous variation to the stoichiometry of protein-ligand complexes
    • Ingham, K. C. On the application of Job's method of continuous variation to the stoichiometry of protein-ligand complexes. Anal. Biochem. 68, 660-663 (1975).
    • (1975) Anal. Biochem. , vol.68 , pp. 660-663
    • Ingham, K.C.1
  • 49
    • 0029559848 scopus 로고
    • Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule
    • Soai, K., Shibata, T., Morioka, H. & Choji, K. Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule. Nature 378, 767-768 (1995).
    • (1995) Nature , vol.378 , pp. 767-768
    • Soai, K.1    Shibata, T.2    Morioka, H.3    Choji, K.4
  • 50
    • 33745248399 scopus 로고    scopus 로고
    • Thermodynamic control of asymmetric amplification in amino acid catalysis
    • Klussmann, M. et al. Thermodynamic control of asymmetric amplification in amino acid catalysis. Nature 441, 621-623 (2006).
    • (2006) Nature , vol.441 , pp. 621-623
    • Klussmann, M.1
  • 51
    • 33847330197 scopus 로고    scopus 로고
    • Serine sublimes with spontaneous chiral amplification
    • Perry, R. H., Wu, C., Nefliu, M. & Cooks, R. G. Serine sublimes with spontaneous chiral amplification. Chem. Commun. 1071-1073 (2007).
    • (2007) Chem. Commun. , pp. 1071-1073
    • Perry, R.H.1    Wu, C.2    Nefliu, M.3    Cooks, R.G.4
  • 52
    • 34250766709 scopus 로고    scopus 로고
    • An astrophysically-relevant mechanism for amino acid enantiomer enrichment
    • Fletcher, S. P., Jagt, R. B.C. & Feringa, B. L. An astrophysically-relevant mechanism for amino acid enantiomer enrichment. Chem. Commun. 2578-2580 (2007).
    • (2007) Chem. Commun. , pp. 2578-2580
    • Fletcher, S.P.1    Jagt, R.B.C.2    Feringa, B.L.3
  • 53
    • 22644444387 scopus 로고    scopus 로고
    • Structures, spectral and electrochemical properties of N-(naphth-2-ylmethyl)-appended porphyrinogens
    • Hill, J. P., Schmitt, W., McCarty, A. L., Ariga, K. & D'Souza, F. Structures, spectral and electrochemical properties of N-(naphth-2-ylmethyl)- appended porphyrinogens. Eur. J. Org. Chem. 2893-2902 (2005).
    • (2005) Eur. J. Org. Chem. , pp. 2893-2902
    • Hill, J.P.1    Schmitt, W.2    McCarty, A.L.3    Ariga, K.4    D'Souza, F.5
  • 54
    • 4344606959 scopus 로고    scopus 로고
    • Highly nonplanar, electron deficient, N-substituted tetraoxocyclohexadienylidene porphyrinogens: Structural, computational, and electrochemical investigations
    • Hill, J. P. et al. Highly nonplanar, electron deficient, N-substituted tetraoxocyclohexadienylidene porphyrinogens: structural, computational, and electrochemical investigations. J. Org. Chem. 69, 5861-5869 (2004).
    • (2004) J. Org. Chem. , vol.69 , pp. 5861-5869
    • Hill, J.P.1


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