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Volumn 48, Issue 6, 1996, Pages 225-232

Per-O-methylated α- and β-CD: Cyclodextrins with inverse hydrophobicity[1]

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EID: 0001438692     PISSN: 00389056     EISSN: None     Source Type: Journal    
DOI: 10.1002/star.19960480606     Document Type: Article
Times cited : (19)

References (55)
  • 1
    • 0042038975 scopus 로고    scopus 로고
    • Sucrose as a renewable organic raw material; New, selective entry reactions via computer simulation of its solution conformations and its hydroxyl group reactivities
    • Berlin
    • This account is Part 13 of the series "Molecular Modelling of Saccharides". - Part 12: Lichtenthaler, F. W., P. Pokinskyj, and S. Immel: Sucrose as a renewable organic raw material; New, selective entry reactions via computer simulation of its solution conformations and its hydroxyl group reactivities. Zuckerindustrie (Berlin) 120 (1996), 174-190.
    • (1996) Zuckerindustrie , vol.120 , pp. 174-190
    • Lichtenthaler, F.W.1    Pokinskyj, P.2    Immel, S.3
  • 2
    • 0001157076 scopus 로고
    • Cyclodextrin inclusion compounds in research and industry
    • [2a] Saenger, W.: Cyclodextrin inclusion compounds in research and industry. Angew. Chem. 92 (1980), 343-361; Angew. Chem. Int. Ed. Engl. 19 (1980), 344-362.
    • (1980) Angew. Chem. , vol.92 , pp. 343-361
    • Saenger, W.1
  • 3
    • 84985609923 scopus 로고
    • [2a] Saenger, W.: Cyclodextrin inclusion compounds in research and industry. Angew. Chem. 92 (1980), 343-361; Angew. Chem. Int. Ed. Engl. 19 (1980), 344-362.
    • (1980) Angew. Chem. Int. Ed. Engl. , vol.19 , pp. 344-362
  • 4
    • 0000806772 scopus 로고
    • Structural aspects of cyclodextrins and their inclusion complexes
    • J.L. Atwood, J.E.D. Davies, D.D. MacNicol, Eds., Acad. Press, London
    • [2b] Saenger, W.: Structural aspects of cyclodextrins and their inclusion complexes. In: Inclusion Compounds (J.L. Atwood, J.E.D. Davies, D.D. MacNicol, Eds.), Acad. Press, London, Vol. 2 (1984), pp. 231-259.
    • (1984) Inclusion Compounds , vol.2 , pp. 231-259
    • Saenger, W.1
  • 5
    • 0000219511 scopus 로고
    • Cyclodextrins as building blocks for supramolecular structures and functional units
    • Wenz, G.: Cyclodextrins as building blocks for supramolecular structures and functional units. Angew. Chem. 106 (1994), 85-870; Angew. Chem. Int. Ed. Engl. 33 (1994), 803-822.
    • (1994) Angew. Chem. , vol.106 , pp. 85-870
    • Wenz, G.1
  • 6
    • 33748240878 scopus 로고
    • Wenz, G.: Cyclodextrins as building blocks for supramolecular structures and functional units. Angew. Chem. 106 (1994), 85-870; Angew. Chem. Int. Ed. Engl. 33 (1994), 803-822.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 803-822
  • 7
    • 0000766799 scopus 로고
    • Hydrophobic effects, opinions and facts
    • Blokzijl, W., and J. B. F. N. Engberts: Hydrophobic effects, opinions and facts. Angew. Chem. 105 (1993), 1610-1624; Angew. Chem. Int. Ed. Engl. 32 (1993), 1545-1579.
    • (1993) Angew. Chem. , vol.105 , pp. 1610-1624
    • Blokzijl, W.1    Engberts, J.B.F.N.2
  • 8
    • 33746824856 scopus 로고
    • Blokzijl, W., and J. B. F. N. Engberts: Hydrophobic effects, opinions and facts. Angew. Chem. 105 (1993), 1610-1624; Angew. Chem. Int. Ed. Engl. 32 (1993), 1545-1579.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 1545-1579
  • 9
    • 0028126845 scopus 로고
    • Cyclodextrins, cyclomannins and cyclogalactins with five and six (1→4)-linked sugar units: Comparative assessment of their conformations and hydrophobicity potential profiles
    • Lichtenthaler, F. W., and S. Immel: Cyclodextrins, cyclomannins and cyclogalactins with five and six (1→4)-linked sugar units: comparative assessment of their conformations and hydrophobicity potential profiles. Tetrahedron Asymmetry 5 (1994), 2045-2060.
    • (1994) Tetrahedron Asymmetry , vol.5 , pp. 2045-2060
    • Lichtenthaler, F.W.1    Immel, S.2
  • 10
    • 33749092927 scopus 로고    scopus 로고
    • On the hydrophobic characteristics of cyclodextrins: Computer-aided visualization of molecular lipophilicity patterns
    • Lichtenthaler, F. W., and S. Immel: On the hydrophobic characteristics of cyclodextrins: computer-aided visualization of molecular lipophilicity patterns. Liebigs Ann. Chem. (1996), 27-37.
    • (1996) Liebigs Ann. Chem. , pp. 27-37
    • Lichtenthaler, F.W.1    Immel, S.2
  • 11
    • 0001392580 scopus 로고    scopus 로고
    • Towards understanding formation and stability of cyclodextrin inclusion complexes: Computation and visualization of the lipophilicity patterns
    • Lichtenthaler, F. W., and S. Immel: Towards understanding formation and stability of cyclodextrin inclusion complexes: computation and visualization of the lipophilicity patterns. Starch/Stärke 48 (1996), 145-154.
    • (1996) Starch/Stärke , vol.48 , pp. 145-154
    • Lichtenthaler, F.W.1    Immel, S.2
  • 12
    • 49049127627 scopus 로고
    • Synthesis of chemically modified cyclodextrins
    • Croft, A., and R. A. Bartsch: Synthesis of chemically modified cyclodextrins. Tetrahedron 39 (1983), 1417-1474.
    • (1983) Tetrahedron , vol.39 , pp. 1417-1474
    • Croft, A.1    Bartsch, R.A.2
  • 13
    • 0003073092 scopus 로고
    • A highly stereoselective synthesis of cyclomannohexaose (α-cyclomannin)
    • Mori, M., Y. Ito, andT. Ogawa: A highly stereoselective synthesis of cyclomannohexaose (α-cyclomannin). Carbohydr. Res. 192 (1989), 131-146.
    • (1989) Carbohydr. Res. , vol.192 , pp. 131-146
    • Mori, M.1    Ito, Y.2    Ogawa, T.3
  • 14
    • 0342787864 scopus 로고
    • β-Cycloaltrin, a cyclooligosaccharide consisting of seven α(1-4)-linked altropyranones
    • Fujita, K., H. Shimada, K. Ohta, Y. Nogami, K. Nasu, and T. Koga: β-Cycloaltrin, a cyclooligosaccharide consisting of seven α(1-4)-linked altropyranones. Angew. Chem. 107 (1995), 1783-1784; Angew. Chem. Int. Ed. Engl. 34 (1995), 1621-1622.
    • (1995) Angew. Chem. , vol.107 , pp. 1783-1784
    • Fujita, K.1    Shimada, H.2    Ohta, K.3    Nogami, Y.4    Nasu, K.5    Koga, T.6
  • 15
    • 33748219477 scopus 로고
    • Fujita, K., H. Shimada, K. Ohta, Y. Nogami, K. Nasu, and T. Koga: β-Cycloaltrin, a cyclooligosaccharide consisting of seven α(1-4)-linked altropyranones. Angew. Chem. 107 (1995), 1783-1784; Angew. Chem. Int. Ed. Engl. 34 (1995), 1621-1622.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 1621-1622
  • 16
    • 84983954410 scopus 로고
    • Improved synthesis of 6-deoxy analogs of cycloamyloses
    • Takeo, K., T. Sumitomo, and T. Kuge: Improved synthesis of 6-deoxy analogs of cycloamyloses. Starch/Stärke 26 (1974), 111-118.
    • (1974) Starch/Stärke , vol.26 , pp. 111-118
    • Takeo, K.1    Sumitomo, T.2    Kuge, T.3
  • 17
    • 0002429549 scopus 로고
    • Selective halogenation at primary positions of cyclomaltooligosaccharides
    • Gadelle, A., and J. Defaye: Selective halogenation at primary positions of cyclomaltooligosaccharides. Angew. Chem. 103 (1991), 94-96; Angew. Chem. Int. Ed. Engl. 30 (1991), 78-80.
    • (1991) Angew. Chem. , vol.103 , pp. 94-96
    • Gadelle, A.1    Defaye, J.2
  • 18
    • 0006124744 scopus 로고
    • Gadelle, A., and J. Defaye: Selective halogenation at primary positions of cyclomaltooligosaccharides. Angew. Chem. 103 (1991), 94-96; Angew. Chem. Int. Ed. Engl. 30 (1991), 78-80.
    • (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 78-80
  • 19
    • 0014247078 scopus 로고
    • Synthesis of amino derivatives of α-CD and of raffinose
    • [13a] Umezawa, S., and K. Tatsuta: Synthesis of amino derivatives of α-CD and of raffinose. Bull. Chem. Soc. Jpn. 41 (1968) 464-468.
    • (1968) Bull. Chem. Soc. Jpn. , vol.41 , pp. 464-468
    • Umezawa, S.1    Tatsuta, K.2
  • 20
    • 0000227522 scopus 로고
    • Highly selective sulfonylation of β-CD and synthesis of its pure amino derivatives
    • [13b] Tsujihara, K., H. Kurita, and M. Kawazu: Highly selective sulfonylation of β-CD and synthesis of its pure amino derivatives. Bull. Chem. Soc. Jpn. 50 (1977), 1567-1571.
    • (1977) Bull. Chem. Soc. Jpn. , vol.50 , pp. 1567-1571
    • Tsujihara, K.1    Kurita, H.2    Kawazu, M.3
  • 21
    • 0346542305 scopus 로고
    • Selective modification of all primary hydroxyl group of α- and β-cyclodextrin
    • [13c] Boger, J., R. J. Corcoran, and J. M. Lehn: Selective modification of all primary hydroxyl group of α- and β-cyclodextrin. Helv. Chim. Acta 61 (1978), 2190-2218.
    • (1978) Helv. Chim. Acta , vol.61 , pp. 2190-2218
    • Boger, J.1    Corcoran, R.J.2    Lehn, J.M.3
  • 23
    • 49049134955 scopus 로고
    • Crystal and molecular structure of β-CD dodecahydrate
    • Lindner, K., and W. Saenger: Crystal and molecular structure of β-CD dodecahydrate. Carbohydr. Res. 99 (1982), 103-115.
    • (1982) Carbohydr. Res. , vol.99 , pp. 103-115
    • Lindner, K.1    Saenger, W.2
  • 24
  • 26
    • 6044241259 scopus 로고
    • [16b] Coleman, A. W., M. Munoz, H. Parrot-Lopez, P. Prognon, J.-M. Valleton, A. Baszkin, S. Alexandre, F. Sommer, T. Minh-Duc, and D. Wonessidjewe: Tailoring cyclodextrins for the construction of large scale molecular assemblies. NATO ASI Series, Ser. C. 456 (1995), 77-97; Chem. Abstr. 123 (1995), 83863r.
    • (1995) Chem. Abstr. , vol.123
  • 27
    • 49949124433 scopus 로고
    • Conformation of O-methylated amyloses and cyclodextrins
    • Casu, B., M. Reggiani, G. G. Gallo, and A. Vigevani: Conformation of O-methylated amyloses and cyclodextrins. Tetrahedron 24 (1968), 803-821.
    • (1968) Tetrahedron , vol.24 , pp. 803-821
    • Casu, B.1    Reggiani, M.2    Gallo, G.G.3    Vigevani, A.4
  • 28
    • 0001363644 scopus 로고
    • Recent advances in the X-ray analysis of cyclodextrin complexes
    • J. L. Atwood, J. E. D. Davies, D. D. MacNicol, Eds., Oxford Univ. Press, Oxford, UK
    • Harata, K.: Recent advances in the X-ray analysis of cyclodextrin complexes. In: Inclusion Compounds (J. L. Atwood, J. E. D. Davies, D. D. MacNicol, Eds.), Oxford Univ. Press, Oxford, UK, Vol. 5 (1991), pp. 311-344.
    • (1991) Inclusion Compounds , vol.5 , pp. 311-344
    • Harata, K.1
  • 29
    • 0000769788 scopus 로고
    • Topography of cyclodextrin inclusion complexes, VI. The crystal and molecular structure of α-cyclodextrin-p-iodoaniline trihydrate
    • Sect. B
    • [19a] Saenger, W., K. Beyer, and P. C. Manor: Topography of cyclodextrin inclusion complexes, VI. The crystal and molecular structure of α-cyclodextrin-p-iodoaniline trihydrate. Acta Crystallogr., Sect. B 32 (1976), 120-128.
    • (1976) Acta Crystallogr. , vol.32 , pp. 120-128
    • Saenger, W.1    Beyer, K.2    Manor, P.C.3
  • 30
    • 0040143005 scopus 로고
    • The structure of the cyclodextrin complex, XI. Crystal structure of hexakis-(2,3,6-tri-O-methyl)-α-cyclodextrin p-iodoaniline monohydrate
    • [19b] Harata, K., K. Uekama, M. Otagiri, and F. Hirayama: The structure of the cyclodextrin complex, XI. Crystal structure of hexakis-(2,3,6-tri-O-methyl)-α-cyclodextrin p-iodoaniline monohydrate. Bull. Chem. Soc. Jpn. 55 (1982), 407-410.
    • (1982) Bull. Chem. Soc. Jpn. , vol.55 , pp. 407-410
    • Harata, K.1    Uekama, K.2    Otagiri, M.3    Hirayama, F.4
  • 31
    • 85010105963 scopus 로고    scopus 로고
    • Crystal structures of α-cyclodextrin-3-iodopropionic acid (1:1) complex pentahydrate and hexakis(2,3,6-tri-O-methyl)-α-cyclodextrin iodoacetic acid (1:1) complex monohydrate
    • [20a] Harata, K., K. Uekama, M. Otagiri, and F. Hirayama: Crystal structures of α-cyclodextrin-3-iodopropionic acid (1:1) complex pentahydrate and hexakis(2,3,6-tri-O-methyl)-α-cyclodextrin iodoacetic acid (1:1) complex monohydrate. Nippon Kagaku Kaishi 1983,173-180; Chem. Abstr. 98 (1983), 135604 u.
    • Nippon Kagaku Kaishi , vol.1983 , pp. 173-180
    • Harata, K.1    Uekama, K.2    Otagiri, M.3    Hirayama, F.4
  • 32
    • 85010105963 scopus 로고    scopus 로고
    • [20a] Harata, K., K. Uekama, M. Otagiri, and F. Hirayama: Crystal structures of α-cyclodextrin-3-iodopropionic acid (1:1) complex pentahydrate and hexakis(2,3,6-tri-O-methyl)-α-cyclodextrin iodoacetic acid (1:1) complex monohydrate. Nippon Kagaku Kaishi 1983,173-180; Chem. Abstr. 98 (1983), 135604 u.
    • (1983) Chem. Abstr. , vol.98
  • 33
    • 0343553161 scopus 로고
    • Crystal structure of the inclusion complex of hexakis-(2,6-di-O-methyl)-cyclomaltohexaose with 3-iodopropionic acid
    • [20b] Harata, K.: Crystal structure of the inclusion complex of hexakis-(2,6-di-O-methyl)-cyclomaltohexaose with 3-iodopropionic acid. Carbohydr. Res. 192 (1989), 33-42.
    • (1989) Carbohydr. Res. , vol.192 , pp. 33-42
    • Harata, K.1
  • 34
    • 0001153254 scopus 로고
    • The structure of the cyclodextrin complex, X. Crystal structure of α-cyclodextrin benzaldehyde (1:1) complex hexahydrate
    • [21a] Harata, K., K. Uekama, M. Otagiri, F. Hirayama, and H. Ogino: The structure of the cyclodextrin complex, X. Crystal structure of α-cyclodextrin benzaldehyde (1:1) complex hexahydrate. Bull. Chem. Soc. Jpn. 54 (1981), 1954-1959.
    • (1981) Bull. Chem. Soc. Jpn. , vol.54 , pp. 1954-1959
    • Harata, K.1    Uekama, K.2    Otagiri, M.3    Hirayama, F.4    Ogino, H.5
  • 35
    • 0009361072 scopus 로고
    • The structure of the cyclodextrin complex, XIV. Crystal structure of hexakis-(2,3,6-tri-O-methyl)-α-cyclodextrin benzaldehyde (1:1) complex
    • [21b] Harata, K., K. Uekama, M. Otagiri, F. Hirayama, and Y. Sugiyama: The structure of the cyclodextrin complex, XIV. Crystal structure of hexakis-(2,3,6-tri-O-methyl)-α-cyclodextrin benzaldehyde (1:1) complex. Bull. Chem. Soc. Jpn. 55 (1982), 3386-3389.
    • (1982) Bull. Chem. Soc. Jpn. , vol.55 , pp. 3386-3389
    • Harata, K.1    Uekama, K.2    Otagiri, M.3    Hirayama, F.4    Sugiyama, Y.5
  • 36
    • 0000657880 scopus 로고
    • The structure of the cyclodextrin complex, V. Crystal structure of α-cyclodextrin complexes with p-nitrophenol and p-hydroxybenzoic acid
    • [22a] Harata, K.: The structure of the cyclodextrin complex, V. Crystal structure of α-cyclodextrin complexes with p-nitrophenol and p-hydroxybenzoic acid. Bull. Chem. Soc. Jpn. 50 (1977), 1416-1424.
    • (1977) Bull. Chem. Soc. Jpn. , vol.50 , pp. 1416-1424
    • Harata, K.1
  • 37
    • 0000556708 scopus 로고
    • The structure of the cyclodextrin complex, XV. Crystal structure of hexakis-(2,3,6-tri-O-methyl)-α-cyclodextrin p-nitrophenol (1:1) complex monohydrate
    • [22b] Harata, K., K. Uekama, M. Otagiri, and F. Hirayama: The structure of the cyclodextrin complex, XV. Crystal structure of hexakis-(2,3,6-tri-O-methyl)-α-cyclodextrin p-nitrophenol (1:1) complex monohydrate. Bull. Chem. Soc. Jpn. 55 (1982), 3904-3910.
    • (1982) Bull. Chem. Soc. Jpn. , vol.55 , pp. 3904-3910
    • Harata, K.1    Uekama, K.2    Otagiri, M.3    Hirayama, F.4
  • 38
    • 37049072859 scopus 로고
    • Role of hydrogen bond and spatial fitting in the chiral recognition by cyclodextrins
    • Harata, K.: Role of hydrogen bond and spatial fitting in the chiral recognition by cyclodextrins. J. Chem. Soc., Perkin Trans. 2 (1990), 799-804.
    • (1990) J. Chem. Soc., Perkin Trans. 2 , pp. 799-804
    • Harata, K.1
  • 39
    • 0000367353 scopus 로고
    • Gaschromatographic separation of enantiomers on cyclodextrin derivatives
    • Schurig, V., and H. P. Novotny: Gaschromatographic separation of enantiomers on cyclodextrin derivatives. Angew. Chem. 102 (1990), 969-986; Angew. Chem. Int. Ed. Engl. 29 (1990), 939-958.
    • (1990) Angew. Chem. , vol.102 , pp. 969-986
    • Schurig, V.1    Novotny, H.P.2
  • 40
    • 0025006411 scopus 로고
    • Schurig, V., and H. P. Novotny: Gaschromatographic separation of enantiomers on cyclodextrin derivatives. Angew. Chem. 102 (1990), 969-986; Angew. Chem. Int. Ed. Engl. 29 (1990), 939-958.
    • (1990) Angew. Chem. Int. Ed. Engl. , vol.29 , pp. 939-958
  • 41
    • 5244375665 scopus 로고
    • Crystal structures of heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin complexes with (R)- and (S)-fluorbiprofen
    • Harata, A., K. Uekama, T. Imai, F. Hirayama, and M. Otagiri: Crystal structures of heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin complexes with (R)- and (S)-fluorbiprofen. J. Incl. Phenom. 6 (1988), 443-460.
    • (1988) J. Incl. Phenom. , vol.6 , pp. 443-460
    • Harata, A.1    Uekama, K.2    Imai, T.3    Hirayama, F.4    Otagiri, M.5
  • 43
    • 1842692143 scopus 로고
    • A general definition of ring puckering coordinates
    • [27a] Cremer, D., and J. A. Pople: A general definition of ring puckering coordinates. J. Am. Chem. Soc. 97 (1975), 1354-1358.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 1354-1358
    • Cremer, D.1    Pople, J.A.2
  • 44
    • 0000452754 scopus 로고
    • Stereographic representation of the Cremer-Pople ring puckering parameters for pyranoid rings
    • [27b] Jeffrey, G. A., and J. H. Yates: Stereographic representation of the Cremer-Pople ring puckering parameters for pyranoid rings. Carbohydr. Res. 74 (1979), 319-322.
    • (1979) Carbohydr. Res. , vol.74 , pp. 319-322
    • Jeffrey, G.A.1    Yates, J.H.2
  • 46
    • 0042968031 scopus 로고
    • Molecular graphics - How to see a molecular scenario with the eyes of a molecule
    • [28b] Brickmann, J.: Molecular graphics - how to see a molecular scenario with the eyes of a molecule. J. Chim. Phys. 89 (1992), 1709-1721.
    • (1992) J. Chim. Phys. , vol.89 , pp. 1709-1721
    • Brickmann, J.1
  • 47
    • 0002328970 scopus 로고    scopus 로고
    • MOLCAD - Computer-aided visualization and manipulation of models in molecular science
    • Eds.: F. H. Post, A. J. S. Hin, Springer, Heidelberg
    • [28c] Waldherr-Teschner, M., T. Goetze, W. Heiden, M. Knoblauch, H. Vollhardt, and J. Brickmann: MOLCAD - Computer-aided visualization and manipulation of models in molecular science. In: Advances in Scientific Visualization (Eds.: F. H. Post, A. J. S. Hin), Springer, Heidelberg 1992, pp. 58-67.
    • Advances in Scientific Visualization , vol.1992 , pp. 58-67
    • Waldherr-Teschner, M.1    Goetze, T.2    Heiden, W.3    Knoblauch, M.4    Vollhardt, H.5    Brickmann, J.6
  • 49
    • 0027673371 scopus 로고
    • A new approach to analysis and display of local lipophilicity/hydrophilicity mapped on molecular surfaces (MLP)
    • [29a] Heiden, W., G. Moeckel, and J. Brickmann: A new approach to analysis and display of local lipophilicity/hydrophilicity mapped on molecular surfaces (MLP). J. Comput.-Aided Mol. Des. 7 (1993), 503-514.
    • (1993) J. Comput.-Aided Mol. Des. , vol.7 , pp. 503-514
    • Heiden, W.1    Moeckel, G.2    Brickmann, J.3
  • 54
    • 11644328584 scopus 로고
    • Systematic analysis of structural data as a research technique in organic chemistry
    • [31c] Allen, F. H., O. Kennard, and R. Taylor: Systematic analysis of structural data as a research technique in organic chemistry. Acc. Chem. Res. 16 (1983), 146-153.
    • (1983) Acc. Chem. Res. , vol.16 , pp. 146-153
    • Allen, F.H.1    Kennard, O.2    Taylor, R.3


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