메뉴 건너뛰기




Volumn 4, Issue 12, 1998, Pages 2523-2531

Cyclodextrin-scaffolded glycoclusters

Author keywords

Clusters; Cyclodextrins; Glycoclusters; Glycosyl isothiocyanates; Glycosylthioureas

Indexed keywords

AMINOSUGAR; CELLOBIOSE; CYCLODEXTRIN; GLYCOPYRANOSIDE; ISOTHIOCYANIC ACID DERIVATIVE; THIOUREA DERIVATIVE;

EID: 0031773651     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19981204)4:12<2523::AID-CHEM2523>3.0.CO;2-2     Document Type: Article
Times cited : (65)

References (71)
  • 2
    • 0001094662 scopus 로고    scopus 로고
    • b) R. Dwek, Chem. Rev. 1996, 96, 683-720;
    • (1996) Chem. Rev. , vol.96 , pp. 683-720
    • Dwek, R.1
  • 6
    • 0002436277 scopus 로고    scopus 로고
    • Eds.: H.-J. Gabius, S. Gabius, Chapman & Hall, Weinheim
    • b) N. V. Bovin in Glycosciences, Status and Perspectives (Eds.: H.-J. Gabius, S. Gabius), Chapman & Hall, Weinheim, 1997, pp. 277-289;
    • (1997) Glycosciences, Status and Perspectives , pp. 277-289
    • Bovin, N.V.1
  • 10
  • 19
    • 0002107732 scopus 로고    scopus 로고
    • Ed.: G.-J. Boons, Blackie Academic & Professional, London
    • (g) R. Roy, in Carbohydrate Chemistry (Ed.: G.-J. Boons), Blackie Academic & Professional, London, 1998, pp. 243-321.
    • (1998) Carbohydrate Chemistry , pp. 243-321
    • Roy, R.1
  • 20
    • 0031239051 scopus 로고    scopus 로고
    • and references therein
    • For noteworthy examples see: a) R. T. Lee, Y. C. Lee, Bioconjugate Chem. 1997, 8, 762-765, and references therein; b) U. Sprengard, M. Schudok, W. Schmidt, G. Kretzschmar, H. Kunz, Angew. Chem. 1996, 108, 359-362; Angew. Chem. Int. Ed. Engl. 1996, 35, 321-324.
    • (1997) Bioconjugate Chem. , vol.8 , pp. 762-765
    • Lee, R.T.1    Lee, Y.C.2
  • 21
    • 0001457502 scopus 로고    scopus 로고
    • For noteworthy examples see: a) R. T. Lee, Y. C. Lee, Bioconjugate Chem. 1997, 8, 762-765, and references therein; b) U. Sprengard, M. Schudok, W. Schmidt, G. Kretzschmar, H. Kunz, Angew. Chem. 1996, 108, 359-362; Angew. Chem. Int. Ed. Engl. 1996, 35, 321-324.
    • (1996) Angew. Chem. , vol.108 , pp. 359-362
    • Sprengard, U.1    Schudok, M.2    Schmidt, W.3    Kretzschmar, G.4    Kunz, H.5
  • 22
    • 33748232917 scopus 로고    scopus 로고
    • For noteworthy examples see: a) R. T. Lee, Y. C. Lee, Bioconjugate Chem. 1997, 8, 762-765, and references therein; b) U. Sprengard, M. Schudok, W. Schmidt, G. Kretzschmar, H. Kunz, Angew. Chem. 1996, 108, 359-362; Angew. Chem. Int. Ed. Engl. 1996, 35, 321-324.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 321-324
  • 23
    • 0003799567 scopus 로고    scopus 로고
    • Ed.: G.-J. Boons, Blackie Academic & Professional, London
    • a) S. A. Nepogodiev, J. F. Stoddart, in Carbohydrate Chemistry (Ed.: G.-J. Boons), Blackie Academic & Professional, London, 1998, pp. 322-383;
    • (1998) Carbohydrate Chemistry , pp. 322-383
    • Nepogodiev, S.A.1    Stoddart, J.F.2
  • 25
    • 33748240878 scopus 로고
    • c) G. Wenz, Angew. Chem. 1994, 106, 851; Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822.
    • (1994) Angew. Chem. , vol.106 , pp. 851
    • Wenz, G.1
  • 26
    • 33748240878 scopus 로고
    • c) G. Wenz, Angew. Chem. 1994, 106, 851; Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 803-822
  • 29
    • 0344515252 scopus 로고    scopus 로고
    • J. Defaye, C. Ortiz Mellet, J. M. García Fernández (CNRS), WO 9733919, FR 96-3221, 1996 [Chem. Abstr. 1997, 127, 264489].
    • (1997) Chem. Abstr. , vol.127 , pp. 264489
  • 30
    • 0028672765 scopus 로고
    • For general reviews see: a) C. M. Reichert, C. E. Hayes, I. J. Goldstein, Methods Enzymol. 1994, 242, 108-116; b) E. Kallin, Methods Enzymol. 1994, 242, 119-123; c) C. R. McBroom, C. H. Samanen, I. J. Goldstein, Methods Enzymol. 1972, 28B, 212-219.
    • (1994) Methods Enzymol. , vol.242 , pp. 108-116
    • Reichert, C.M.1    Hayes, C.E.2    Goldstein, I.J.3
  • 31
    • 0028674287 scopus 로고
    • For general reviews see: a) C. M. Reichert, C. E. Hayes, I. J. Goldstein, Methods Enzymol. 1994, 242, 108-116; b) E. Kallin, Methods Enzymol. 1994, 242, 119-123; c) C. R. McBroom, C. H. Samanen, I. J. Goldstein, Methods Enzymol. 1972, 28B, 212-219.
    • (1994) Methods Enzymol. , vol.242 , pp. 119-123
    • Kallin, E.1
  • 32
    • 0000597927 scopus 로고
    • For general reviews see: a) C. M. Reichert, C. E. Hayes, I. J. Goldstein, Methods Enzymol. 1994, 242, 108-116; b) E. Kallin, Methods Enzymol. 1994, 242, 119-123; c) C. R. McBroom, C. H. Samanen, I. J. Goldstein, Methods Enzymol. 1972, 28B, 212-219.
    • (1972) Methods Enzymol. , vol.28 B , pp. 212-219
    • McBroom, C.R.1    Samanen, C.H.2    Goldstein, I.J.3
  • 33
    • 0000792507 scopus 로고    scopus 로고
    • a) T. K. Lindhorst, C. Kieburg, Angew. Chem. 1996, 108, 2083-2086; Angew. Chem. Int. Ed. Engl. 1996, 35, 1953-1956;
    • (1996) Angew. Chem. , vol.108 , pp. 2083-2086
    • Lindhorst, T.K.1    Kieburg, C.2
  • 34
    • 0029911174 scopus 로고    scopus 로고
    • a) T. K. Lindhorst, C. Kieburg, Angew. Chem. 1996, 108, 2083-2086; Angew. Chem. Int. Ed. Engl. 1996, 35, 1953-1956;
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1953-1956
  • 42
    • 0030831718 scopus 로고    scopus 로고
    • Recently, the preparation of several calixarene - carbohydrate structures, called calixsugars, endowed with similar features has been reported. See: a) A. Dondoni, A. Marra, M C. Scherrmann, A. Casnati, F. Sansone, R. Ungaro, Chem. Eur. J. 1997, 3, 1774-1782; b) A. Dondoni, M. Kleban, A. Marra, Tetrahedron Lett. 1997, 38, 7801-7804; c) A. Marra, A. Dondoni, F. Sansone, J. Org. Chem. 1996, 61, 5155-5158; d) S. J. Meunier, R. Roy, Tetrahedron Lett. 1996, 37, 7801-7804; e) A. Marra, M C. Scherrmann, A. Dondoni, A. Casnati, P. Minari, R. Ungaro, Angew. Chem. 1994, 106, 2533; Angew. Chem. Int. Ed. Engl. 1994, 33, 2479-2481.
    • (1997) Chem. Eur. J. , vol.3 , pp. 1774-1782
    • Dondoni, A.1    Marra, A.2    Scherrmann, M.C.3    Casnati, A.4    Sansone, F.5    Ungaro, R.6
  • 43
    • 0030710979 scopus 로고    scopus 로고
    • Recently, the preparation of several calixarene - carbohydrate structures, called calixsugars, endowed with similar features has been reported. See: a) A. Dondoni, A. Marra, M C. Scherrmann, A. Casnati, F. Sansone, R. Ungaro, Chem. Eur. J. 1997, 3, 1774-1782; b) A. Dondoni, M. Kleban, A. Marra, Tetrahedron Lett. 1997, 38, 7801-7804; c) A. Marra, A. Dondoni, F. Sansone, J. Org. Chem. 1996, 61, 5155-5158; d) S. J. Meunier, R. Roy, Tetrahedron Lett. 1996, 37, 7801-7804; e) A. Marra, M C. Scherrmann, A. Dondoni, A. Casnati, P. Minari, R. Ungaro, Angew. Chem. 1994, 106, 2533; Angew. Chem. Int. Ed. Engl. 1994, 33, 2479-2481.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 7801-7804
    • Dondoni, A.1    Kleban, M.2    Marra, A.3
  • 44
    • 0030017406 scopus 로고    scopus 로고
    • Recently, the preparation of several calixarene - carbohydrate structures, called calixsugars, endowed with similar features has been reported. See: a) A. Dondoni, A. Marra, M C. Scherrmann, A. Casnati, F. Sansone, R. Ungaro, Chem. Eur. J. 1997, 3, 1774-1782; b) A. Dondoni, M. Kleban, A. Marra, Tetrahedron Lett. 1997, 38, 7801-7804; c) A. Marra, A. Dondoni, F. Sansone, J. Org. Chem. 1996, 61, 5155-5158; d) S. J. Meunier, R. Roy, Tetrahedron Lett. 1996, 37, 7801-7804; e) A. Marra, M C. Scherrmann, A. Dondoni, A. Casnati, P. Minari, R. Ungaro, Angew. Chem. 1994, 106, 2533; Angew. Chem. Int. Ed. Engl. 1994, 33, 2479-2481.
    • (1996) J. Org. Chem. , vol.61 , pp. 5155-5158
    • Marra, A.1    Dondoni, A.2    Sansone, F.3
  • 45
    • 3743091591 scopus 로고    scopus 로고
    • Recently, the preparation of several calixarene - carbohydrate structures, called calixsugars, endowed with similar features has been reported. See: a) A. Dondoni, A. Marra, M C. Scherrmann, A. Casnati, F. Sansone, R. Ungaro, Chem. Eur. J. 1997, 3, 1774-1782; b) A. Dondoni, M. Kleban, A. Marra, Tetrahedron Lett. 1997, 38, 7801-7804; c) A. Marra, A. Dondoni, F. Sansone, J. Org. Chem. 1996, 61, 5155-5158; d) S. J. Meunier, R. Roy, Tetrahedron Lett. 1996, 37, 7801-7804; e) A. Marra, M C. Scherrmann, A. Dondoni, A. Casnati, P. Minari, R. Ungaro, Angew. Chem. 1994, 106, 2533; Angew. Chem. Int. Ed. Engl. 1994, 33, 2479-2481.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7801-7804
    • Meunier, S.J.1    Roy, R.2
  • 46
    • 0000403668 scopus 로고
    • Recently, the preparation of several calixarene - carbohydrate structures, called calixsugars, endowed with similar features has been reported. See: a) A. Dondoni, A. Marra, M C. Scherrmann, A. Casnati, F. Sansone, R. Ungaro, Chem. Eur. J. 1997, 3, 1774-1782; b) A. Dondoni, M. Kleban, A. Marra, Tetrahedron Lett. 1997, 38, 7801-7804; c) A. Marra, A. Dondoni, F. Sansone, J. Org. Chem. 1996, 61, 5155-5158; d) S. J. Meunier, R. Roy, Tetrahedron Lett. 1996, 37, 7801-7804; e) A. Marra, M C. Scherrmann, A. Dondoni, A. Casnati, P. Minari, R. Ungaro, Angew. Chem. 1994, 106, 2533; Angew. Chem. Int. Ed. Engl. 1994, 33, 2479-2481.
    • (1994) Angew. Chem. , vol.106 , pp. 2533
    • Marra, A.1    Scherrmann, M.C.2    Dondoni, A.3    Casnati, A.4    Minari, P.5    Ungaro, R.6
  • 47
    • 33751130579 scopus 로고
    • Recently, the preparation of several calixarene - carbohydrate structures, called calixsugars, endowed with similar features has been reported. See: a) A. Dondoni, A. Marra, M C. Scherrmann, A. Casnati, F. Sansone, R. Ungaro, Chem. Eur. J. 1997, 3, 1774-1782; b) A. Dondoni, M. Kleban, A. Marra, Tetrahedron Lett. 1997, 38, 7801-7804; c) A. Marra, A. Dondoni, F. Sansone, J. Org. Chem. 1996, 61, 5155-5158; d) S. J. Meunier, R. Roy, Tetrahedron Lett. 1996, 37, 7801-7804; e) A. Marra, M C. Scherrmann, A. Dondoni, A. Casnati, P. Minari, R. Ungaro, Angew. Chem. 1994, 106, 2533; Angew. Chem. Int. Ed. Engl. 1994, 33, 2479-2481.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 2479-2481
  • 51
    • 33748241612 scopus 로고
    • d) A. Gadelle, J. Defaye, Angew. Chem. 1991, 103, 94; Angew. Chem. Int. Ed. Engl. 1991, 30, 78-80.
    • (1991) Angew. Chem. , vol.103 , pp. 94
    • Gadelle, A.1    Defaye, J.2
  • 52
    • 33748241612 scopus 로고
    • d) A. Gadelle, J. Defaye, Angew. Chem. 1991, 103, 94; Angew. Chem. Int. Ed. Engl. 1991, 30, 78-80.
    • (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 78-80
  • 58
    • 3743139515 scopus 로고    scopus 로고
    • note
    • The saponification step is cruxial in the synthetic scheme. After treatment of a methanolic solution of the conjugates with sodium methoxyde, a precipitate containing a mixture of partially protected derivatives was formed. Addition of water allowed isolation of the fully unprotected compounds as the sole reaction products.
  • 59
    • 0030852402 scopus 로고    scopus 로고
    • The use of fully unprotected sugar isothiocyanate conjugates in the preparation of carbohydrate-coated PAMAM-based dendrimers has recently been reported by Kieburg and Linhorst (c.f. ref. [10b]). A different strategy, using amino sugar conjugates and the amide bond forming methodology, has also been reported (c.f. N. Jayaraman, J. F. Stoddart, Tetrahedron Lett. 1997, 38, 6767-6770).
    • (1997) Tetrahedron Lett. , vol.38 , pp. 6767-6770
    • Jayaraman, N.1    Stoddart, J.F.2
  • 60
    • 3743113842 scopus 로고    scopus 로고
    • note
    • 2O, 343 K). Since FABMS and microanalytical data agreed with the expected values, an isomerisation reaction, likely at the anomeric center, probably occurred. Since unprotected α-D-mannopyranosylthiourea-coated glycodendrimers have been already reported (c.f., Linhorst et al., refs [10a, c]), this aspect is currently the object of a detailed investigation in collaboration with Dr. Linhorst (Hamburg University, Germany).
  • 63
    • 0000507418 scopus 로고
    • 1D TOCSY and 2D COSY and HMQC experiments, as well as data for model pseudooligosaccharides obtained by coupling reactions of glycosyl isothiocyanates 6-8 with methyl 6-amino-6-deoxy-α-D-glucopyranoside (c.f., J. M. García Fernández, C. Ortiz Mellet, J. Fuentes, J. Org. Chem. 1993, 55, 5192-5199), were used to assess in NMR assignments.
    • (1993) J. Org. Chem. , vol.55 , pp. 5192-5199
    • García Fernández, J.M.1    Ortiz Mellet, C.2    Fuentes, J.3
  • 69
    • 3743065992 scopus 로고
    • -1 was estimated for the complex Taxotère-19 from extraction experiments at 25 °C.
    • (1995) Chem. Abstr. , vol.123
  • 70
    • 3743057050 scopus 로고    scopus 로고
    • Hemolysis tests were performed by Dr M. Bost at the Hematology Department of the Centre Hospitalier Universitaire de Grenoble. For experimental details, see ref. 12
    • Hemolysis tests were performed by Dr M. Bost at the Hematology Department of the Centre Hospitalier Universitaire de Grenoble. For experimental details, see ref. 12.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.