SCOPUS 정보 검색 플랫폼

Volumn 67, Issue 14, 2002, Pages 4722-4733

Glycoside-clustering round calixarenes toward the development of multivalent carbohydrate ligands. Synthesis and conformational analysis of calix[4]arene O- and C-glycoconjugates

(5) Dondoni, Alessandro a Kleban, Martin a Hu, Xubo a Marra, Alberto a Banks, Harold D b

a UNIVERSITY OF FERRARA (Italy)

b EDGEWOOD CHEMICAL BIOLOGICAL CENTER (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR MECHANICS;

ALCOHOLS; ALDEHYDES; BIOSYNTHESIS; CONFORMATIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REDUCTION; STEREOCHEMISTRY;

OLEFINS;

ALDEHYDE; ALKENE DERIVATIVE; ALKYL GROUP; CALIX[4]ARENE GLYCOSIDE DERIVATIVE; CALIXARENE; CALIXARENE DERIVATIVE; CARBOHYDRATE; PHOSPHORANE DERIVATIVE; POLYOL; TETRAPROPOXYCALIX[4]ARENE DERIVATIVE; UNCLASSIFIED DRUG; CALIX(4)ARENE; GLYCOSIDE; IONOPHORE; LIGAND; PHENOL DERIVATIVE;

ARTICLE; CALCULATION; CARBOHYDRATE ANALYSIS; CHEMICAL BINDING; CHEMICAL STRUCTURE; CONFORMATION; CONJUGATION; GAS ANALYSIS; GLYCOSYLATION; LIGAND BINDING; METHODOLOGY; MOLECULAR MECHANICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; REDUCTION; STRUCTURE ANALYSIS; SYNTHESIS; CATALYSIS; CHEMISTRY; ORGANIC CHEMISTRY;

CATALYSIS; CHEMISTRY, ORGANIC; GLYCOSIDES; GLYCOSYLATION; IONOPHORES; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PHENOLS; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, NON-P.H.S.; CALIXARENES;

EID: 0037067401 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo020178z Document Type: Article

Times cited : (60)

References (113)

1
- 33748539998
- (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 713
- Böhmer, A.¹

2
- 0000526093
- (1995) Bull. Chem. Soc. Jpn. , vol.68 , pp. 1088
- Shinkai, S.¹ Takeshita, M.²

3
- 11944249769
- (1995) Aldrichimica Acta , vol.28 , pp. 3
- Gutsche, C.D.¹

4
- 0012694411
- (1997) Chem. Rev. , vol.97 , pp. 1713
- Ikeda, A.¹ Shinkai, S.²

5
- 0004268367
- The Royal Society of Chemistry, Cambridge
- (1998) Calixarenes Revisited
- Gutsche, C.D.¹

6
- 33751130579
- (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 2479
- Marra, A.¹ Scherrmann, M.-C.² Dondoni, A.³ Casnati, A.⁴ Minari, P.⁵ Ungaro, R.⁶

7
- 0030017406
- (1996) J. Org. Chem. , vol.61 , pp. 5155
- Marra, A.¹ Dondoni, A.² Sansone, F.³

8
- 0030831718
- (1997) Chem. Eur. J. , vol.3 , pp. 1774
- Dondoni, A.¹ Marra, A.² Scherrmann, M.-C.³ Casnati, A.⁴ Sansone, F.⁵ Ungaro, R.⁶

9
- 0030710979
- (1997) Tetrahedron Lett. , vol.38 , pp. 7801
- Dondoni, A.¹ Kleban, M.² Marra, A.³

10
- 0035821225
- (2001) Tetrahedron Lett. , vol.42 , pp. 3295
- Dondoni, A.¹ Hu, X.² Marra, A.³ Banks, H.D.⁴

11
- 0000358206
- (1995) Acc. Chem. Res. , vol.28 , pp. 321
- Lee, Y.C.¹ Lee, R.T.²

12
- 0029434560
- (1995) Essays Biochem. , vol.30 , pp. 59
- Sharon, N.¹ Lis, H.²

13
- 0029001510
- (1995) Annu. Rev. Biochem. , vol.64 , pp. 113
- Lasky, L.A.¹

14
- 0029952519
- (1996) Annu. Rev. Biochem. , vol.65 , pp. 441
- Weis, W.I.¹ Drickamer, K.²

15
- 0032493163
- (1998) Chem. Commun. , pp. 1161
- Sears, P.¹ Wong, C.-H.²

16
- 84911304823
- (1989) Pure Appl. Chem. , vol.61 , pp. 1293
- Quiocho, F.A.¹

17
- 0001906382
- (1991) J. Chem. Rev. , vol.91 , pp. 25
- Glaudemans, C.P.¹

18
- 0027996135
- (1994) Curr. Opin. Struct. Biol. , vol.4 , pp. 719
- Toone, E.J.¹

19
- 0003012148
- (1996) Acc. Chem. Res. , vol.29 , pp. 373
- Lemieux, R.U.¹

20
- 0020046710
- (1982) J. Biol. Chem. , vol.257 , pp. 939
- Connolly, D.T.¹ Townsend, R.R.² Kawaguchi, K.³ Bell, W.R.⁴ Lee, Y.C.⁵

21
- 0021099058
- (1983) J. Biol. Chem. , vol.258 , pp. 199
- Lee, Y.C.¹ Townsend, R.R.² Hardy, M.R.³ Lönngren, J.⁴ Arnap, J.⁵ Haraldsson, M.⁶ Lönn, H.⁷

22
- 0023813272
- (1988) Biochem. Biophys. Res. Commun. , vol.155 , pp. 1444
- Lee, R.T.¹ Lee, Y.C.²

23
- 33746976801
- (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 3215
- Davis, B.G.¹

24
- 0026080794
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 686
- Spaltenstein, A.¹ Whitesides, G.M.²

25
- 0000559057
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 4701
- Glick, G.D.¹ Knowles, J.R.²

26
- 0025738252
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 5865
- Sabesan, S.¹ Duus, J.O.² Domaille, P.³ Kelm, S.⁴ Paulson, J.C.⁵

27
- 0027052956
- (1992) Angew. Chem., Int. Ed. Engl. , vol.31 , pp. 1478
- Roy, R.¹ Andersson, F.K.² Harms, G.³ Kelm, S.⁴ Schauer, R.⁵

28
- 0028273333
- (1994) Antiviral Res. , vol.23 , pp. 179
- Mochalova, L.V.¹ Tuzikov, A.B.² Marinina, V.P.³ Gambaryan, A.S.⁴ Byramova, N.E.⁵ Bovin, N.V.⁶ Matrosovich, M.N.⁷

29
- 0028591816
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 12053
- Mortell, K.H.¹ Gingras, M.² Kiessling, L.L.³

30
- 0029870744
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 2297
- Mortell, K.H.¹ Weatherman, R.V.² Kiessling, L.L.³

31
- 0030250628
- (1996) Chem. Biol. , vol.3 , pp. 757
- Mammen, M.¹ Helmerson, K.² Kishore, R.³ Choi, S.-K.⁴ Phillips, W.D.⁵ Whitesides, G.M.⁶

32
- 0033592057
- (1999) Chem. Commun. , pp. 1557
- Li, Z.-C.¹ Liang, Y.-Z.² Li, F.-M.³

33
- 0028762251
- (1994) Carbohydr. Res. , vol.251 , pp. 285
- Unverzagt, C.¹ Kelm, S.² Paulson, J.C.³

34
- 0028967028
- (1995) Carbohydr. Res. , vol.268 , pp. 17
- Paulsen, H.¹ Peters, S.² Biefeldt, T.³ Meldal, M.⁴ Bock, K.⁵

35
- 33748232917
- (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 321
- Sprengard, U.¹ Schudok, M.² Schmidt, W.³ Kretzschmar, G.⁴ Kunz, H.⁵

36
- 0033620366
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 2662
- Schwarz, J.B.¹ Kuduk, S.D.² Chen, X.-T.³ Sames, D.⁴ Glunz, P.W.⁵ Danishefsky, S.J.⁶

37
- 0035808453
- (2001) Chem. Eur. J. , vol.7 , pp. 230
- Grandjean, C.¹ Gras-Masse, H.² Melnyk, O.³

38
- 0027740240
- (1993) J. Chem. Soc., Chem. Commun. , pp. 1869
- Roy, R.¹ Zanini, D.² Meunier, S.J.³ Romanowska, A.⁴

39
- 0001002781
- (1995) Macromolecules , vol.28 , pp. 5391
- Aoi, K.¹ Itoh, K.² Okada, M.³

40
- 0000439588
- (1996) J. Org. Chem. , vol.61 , pp. 7348
- Zanini, D.¹ Roy, R.²

41
- 28444476615
- (1996) Chem. Eur. J. , vol.2 , pp. 1115
- Ashton, P.R.¹ Boyd, S.E.² Brown, C.L.³ Jayaraman, N.⁴ Nepogodiev, S.A.⁵ Stoddart, J.F.⁶

42
- 0029911174
- (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1953
- Lindhorst, T.K.¹ Kieburg, C.²

43
- 0030971899
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 2088
- Zanini, D.¹ Roy, R.²

44
- 0030974418
- (1997) Chem. Eur. J. , vol.3 , pp. 974
- Ashton, P.R.¹ Boyd, S.E.² Brown, C.L.³ Nepogodiev, S.A.⁴ Meijer, E.W.⁵ Peerlings, H.W.I.⁶ Stoddart, J.F.⁷

45
- 0030803087
- (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 732
- Ashton, P.R.¹ Boyd, S.E.² Brown, C.L.³ Jayaraman, N.⁴ Stoddart, J.F.⁵

46
- 0001574886
- (1998) J. Org. Chem. , vol.63 , pp. 3429
- Ashton, P.R.¹ Hounsell, E.F.² Jayaraman, N.³ Nilsen, T.M.⁴ Spencer, N.⁵ Stoddart, J.F.⁶ Young, M.⁷

47
- 0000378238
- (1998) J. Org. Chem. , vol.63 , pp. 3486
- Zanini, D.¹ Roy, R.²

48
- 0344820766
- (1999) Angew. Chem. Int. Ed. Engl. , vol.38 , pp. 369
- Roy, R.¹ Kim, J.M.²

49
- 85044704201
- (2000) Chembiochem. , vol.1 , pp. 70
- Turnbull, W.B.¹ Pease, A.R.² Stoddart, J.F.³

50
- 0009730838
- (1996) Curr. Opin. Struct. Biol. , vol.6 , pp. 992
- Roy, R.¹

51
- 0030767347
- (1997) Chem. Eur. J. , vol.3 , pp. 1193
- Jayaraman, N.¹ Nepogodiev, S.A.² Stoddart, J.F.³

52
- 0034708750
- (2000) Tetrahedron , vol.56 , pp. 1883
- Budka, J.¹ Tkadlecová, M.² Lhoták, P.³ Stibor, I.⁴

53
- 0030765498
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 6676
- Fujimoto, T.¹ Shimizu, C.² Hayashida, O.³ Aoyama, Y.⁴

54
- 0030983448
- (1997) Tetrahedron Lett. , vol.38 , pp. 4295
- Curtis, A.D.M.¹

55
- 0032573844
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 601
- Fujimoto, T.¹ Shimizu, C.² Hayashida, O.³ Aoyama, Y.⁴

56
- 0033572727
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 11597
- Hayashida, O.¹ Kato, M.² Akagi, K.³ Aoyama, Y.⁴

57
- 0032537072
- (1998) Tetrahedron Lett. , vol.39 , pp. 2307
- König, B.¹ Fricke, T.² Waßmann, A.³ Krallmann-Wenzel, U.⁴ Lindhorst, T.K.⁵

58
- 0032976928
- (1999) Chem. Eur. J. , vol.5 , pp. 1775
- Garcia-López, J.J.¹ Santoyo-González, F.² Vargas-Berenguel, A.³ Giménez-Martinez, J.J.⁴

59
- 0034670567
- (2000) J. Org. Chem. , vol.65 , pp. 8743
- Roy, R.¹ Hernandéz-Mateo, F.² Santoyo-González, F.³

60
- 0034689844
- (2000) Org. Lett. , vol.2 , pp. 1113
- Fulton, D.A.¹ Stoddart, J.F.²

61
- 0026782802
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 7303
- Kingery-Wood, J.E.¹ Williams, K.W.² Sigal, G.B.³ Whitesides, G.M.⁴

62
- 0027467360
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 1146
- Spevak, W.¹ Nagy, J.O.² Charych, D.H.³ Schaefer, M.E.⁴ Gilbert, J.H.⁵ Bednarski, M.D.⁶

63
- 0032546772
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 1524
- Kamitakahara, H.¹ Suzuki, T.² Nishigori, N.³ Suzuki, Y.⁴ Kanie, O.⁵ Wong, C.-H.⁶

64
- 0001403845
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 1587
- Sakai, S.¹ Sasaki, T.²

65
- 0034628502
- (2000) Nature , vol.403 , pp. 669
- Kitov, P.I.¹ Sadowska, J.M.² Mulvey, G.³ Armstrong, G.D.⁴ Ling, H.⁵ Pannu, N.S.⁶ Read, R.J.⁷ Bundle, D.R.⁸

66
- 0034701264
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 2663
- Fan, E.¹ Zhang, Z.² Minke, W.E.³ Hou, Z.⁴ Verlinde, C.L.M.J.⁵ Hol, W.G.J.⁶

67
- 0032476812
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2754
- Mammen, M.¹ Choi, S.-K.² Whitesides, G.M.³

68
- 0032883075
- (1999) Synlett. , pp. 1495
- Davis, B.G.¹ Jones, J.B.²

69
- 0033581586
- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 2978
- Davis, A.P.¹ Wareham, R.S.²

70
- 2742586108
- (1998) Eur. J. Org. Chem. , vol.897
- Sansone, F.¹ Barboso, S.² Casnati, A.³ Fabbi, M.⁴ Pochini, A.⁵ Ugozzoli, F.⁶ Ungaro, R.⁷

71
- 0003042169
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 8
- Park, H.S.¹ Lin, Q.² Hamilton, A.D.³

72
- 0034603097
- (2000) Chem. Eur. J. , vol.6 , pp. 442
- Frkanec, L.¹ Visnjvac, A.² Kojic-Prodic, B.³ Zinic, B.⁴

73
- 0035144021
- (2001) Eur. J. Org. Chem. , pp. 595
- Lazzarotto, M.¹ Sansone, F.² Baldini, L.³ Casnati, A.⁴ Cozzini, P.⁵ Ungaro, R.⁶

74
- 0009660175
- (2001) Synlett , pp. 210
- Beckham Shuker, S.¹ Esterbrook, J.² Gonzalez, J.³

75
- 0030605882
- (1996) Tetrahedron Lett. , vol.37 , pp. 5469
- Meunier, S.J.¹ Roy, R.²

76
- 0032506686
- (1998) Tetrahedron Lett. , vol.39 , pp. 9171
- Félix, C.¹ Parrot-Lopez, H.² Kalchenko, V.³ Coleman, A.W.⁴

77
- 0032715087
- (1999) Synlett , pp. 1891
- Saitz-Barria, C.¹ Torres-Pinedo, A.² Santoyo-Gonzalez, F.³

78
- 0025843516
- (1991) Tetrahedron , vol.47 , pp. 5149
- Marra, A.¹ Gauffeny, F.² Sinay, P.³

79
- 2142765495
- note

80
- 2142696811
- note

81
- 33751553183
- (1990) J. Org. Chem. , vol.55 , pp. 5639
- Van Loon, J.D.¹ Arduini, A.² Coppi, L.³ Verboom, W.⁴ Pochini, A.⁵ Ungaro, R.⁶ Harkema, S.⁷ Reinhoudt, D.N.⁸

82
- 0342541698
- (1985) J. Org. Chem. , vol.50 , pp. 5802
- Gutsche, C.D.¹ Levine, J.A.² Sujeeth, P.K.³

83
- 0001346586
- (1997) J. Org. Chem. , vol.62 , pp. 8114
- Dondoni, A.¹ Zuurmond, H.M.² Boscarato, A.³

84
- 0032558615
- (1998) Tetrahedron Lett. , vol.39 , pp. 7991
- Dondoni, A.¹ Kleban, M.² Zuurmond, H.M.³ Marra, A.⁴

85
- 0034686854
- (2000) Tetrahedron Lett. , vol.41 , pp. 6657
- Dondoni, A.¹ Mizuno, M.² Marra, A.³

86
- 84981848681
- (1966) J. Heterocycl. Chem. , vol.3 , pp. 485
- Leonard, N.J.¹ Carraway, K.L.²

87
- 0000523862
- (1974) Tetrahedron , vol.30 , pp. 3547
- Taniguchi, M.¹ Koga, K.² Yamada, S.³

88
- 2142660333
- note

89
- 0001984365
- (1989) Chem. Lett. , pp. 1747
- Araki, K.¹ Iwamoto, K.² Shinkai, S.³ Matsuda, T.⁴

90
- 21244492862
- (1991) J. Org. Chem. , vol.56 , pp. 4955
- Iwamoto, K.¹ Araki, K.² Shinkai, S.³

91
- 33751154561
- (1995) J. Org. Chem. , vol.60 , pp. 1454
- Arduini, A.¹ Fabbi, M.² Mantovani, M.³ Mirone, L.⁴ Pochini, A.⁵ Secchi, A.⁶ Ungaro, R.⁷

92
- 0032567324
- (1998) J. Org. Chem. , vol.63 , pp. 9872
- Krebs, F.C.¹ Larsen, M.² Jørgensen, M.³ Jensen, P.R.⁴ Bielecki, M.⁵ Schaumburg, K.⁶

93
- 2142696809
- note

94
- 0037681028
- (2000) Chem. Rev. , vol.100 , pp. 4567
- Imberty, A.¹ Pérez, S.²

95
- 84961979616
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 11743
- Callam, C.S.¹ Singer, S.J.² Lowary, T.L.³ Hadad, C.M.⁴

96
- 11944260227
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 4165
- Grootenhuis, P.D.J.¹ Kollman, P.A.² Groenen, L.C.³ Reinhoudt, D.N.⁴ Van Hummel, G.J.⁵ Ugozzoli, F.⁶ Andreetti, G.D.⁷

97
- 33751158643
- (1994) J. Org. Chem. , vol.59 , pp. 1532
- Botta, B.¹ Di Giovanni, M.C.² Delle Monache, G.³ De Rosa, M.C.⁴ Gacs-Baitz, E.⁵ Botta, M.⁶ Corelli, F.⁷ Tafi, A.⁸ Santini, A.⁹ Benedetti, E.¹⁰ Pedone, C.¹¹ Misiti, D.¹²

98
- 0013019514
- (1997) J. Org. Chem. , vol.62 , pp. 932
- Botta, B.¹ Delle Monache, G.² Salvatore, P.³ Gasparrini, F.⁴ Villani, C.⁵ Botta, M.⁶ Corelli, F.⁷ Tafi, A.⁸ Gacs-Baitz, E.⁹ Santini, A.¹⁰ Carvalho, C.F.¹¹ Misiti, D.¹²

99
- 0013019514
- (1997) J. Org. Chem. , vol.62 , pp. 1788
- Botta, B.¹ Delle Monache, G.² De Rosa, M.C.³ Seri, C.⁴ Benedetti, E.⁵ Iacovino, R.⁶ Botta, M.⁷ Corelli, F.⁸ Masignani, V.⁹ Tafi, A.¹⁰ Gacs-Baitz, E.¹¹ Santini, A.¹² Misiti, D.¹³

100
- 0000108358
- (1997) J. Org. Chem. , vol.62 , pp. 3511
- Van Gelder, J.M.¹ Brenn, J.² Thondorf, I.³ Biali, S.E.⁴

101
- 0036156794
- (2002) Chirality , vol.14 , pp. 173
- Banks, H.D.¹ Dondoni, A.² Kleban, M.³ Marra, A.⁴

102
- 0003942864
- Wiley and Sons: New York
- (1994) Stereochemistry of Organic Compounds , pp. 629-630
- Eliel, E.L.¹ Wilen, S.H.² Mander, L.N.³

103
- 0004055425
- Butterworth-Heinemann, Oxford
- (1996) Purification of Laboratory Chemicals, 4th ed.
- Armarego, W.L.F.¹ Perrin, D.D.²

104
- 0002714675
- (1978) J. Org. Chem. , vol.43 , pp. 2923
- Still, W.C.¹ Kahn, M.² Mitra, A.³

105
- 0000913945
- (1992) J. Org. Chem. , vol.57 , pp. 790
- Böhmer, V.¹ Jung, K.² Schön, M.³ Wolff, A.⁴

106
- 33751390792
- (1992) J. Org. Chem. , vol.57 , pp. 4527
- Gutsche, C.D.¹ See, K.A.²

107
- 84982335996
- (1962) Justus Liebigs Ann. Chem. , vol.657 , pp. 179
- Wetgand, F.¹ Ziemann, H.²

108
- 0012335701
- (1998) Ind. J. Chem. B , vol.37 , pp. 252
- Sarbania, S.¹ Roy, N.²

109
- 0001737058
- (1977) J. Org. Chem. , vol.42 , pp. 4084
- Secrist J.A. III¹ Wu, S.-R.²

110
- 33845561484
- (1979) J. Org. Chem. , vol.44 , pp. 1434
- Secrist J.A. III¹ Wu, S.-R.²

111
- 0032546195
- (1998) Tetrahedron , vol.54 , pp. 2827
- Dondoni, A.¹ Marra, A.² Massi, A.³

112
- 84986437005
- (1990) J. Comput. Chem. , vol.11 , pp. 440
- Mohamadi, F.¹ Richards, N.G.J.² Guida, W.C.³ Liskamp, R.⁴ Lipton, M.⁵ Caulfield, C.⁶ Chang, F.⁷ Hendrickson, T.⁸ Still, W.C.⁹

113
- 2142755477
- Spartan Version 5.5.1: Wave function Inc., 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.