SCOPUS 정보 검색 플랫폼

Helvetica Chimica Acta

Volumn 89, Issue 11, 2006, Pages 2591-2610

Synthesis of a potential 10E4 tetrasaccharide antigen involved in scrapie pathogenesis

(4) Bindschädler, Pascal a Noti, Christian a Castagnetti, Eva a Seeberger, Peter H a

a ETH ZURICH (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE LINKERS; GLYCOSYLATION; SCRAPIE PATHOGENESIS; TRAUT'S REAGENTS;

ACIDITY; AMINES; DERIVATIVES; FREE RADICALS; PATHOLOGY; SYNTHESIS (CHEMICAL);

ANTIGENS;

10E4 ANTIGEN; 2 IMINOTHIOLANE; 5 (2 AMINOETHYLSULFONYL)PENTYL (ALPHA LEVO IDOPYRANOSYLURONATE) (1-4) (2 AMINO 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE) (1-4) (BETA DEXTRO GLUCOPYRANOYLURONATE) (1-4) N ACETYL 2 AMINO 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; ANTIGEN; POLYSACCHARIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CRYSTAL STRUCTURE; GLYCOSYLATION; NONHUMAN; PATHOGENESIS; PRIORITY JOURNAL; SCRAPIE;

EID: 33845358027 PISSN: 0018019X EISSN: None Source Type: Journal
DOI: 10.1002/hlca.200690234 Document Type: Article

Times cited : (16)

References (66)

1
- 0026619789
- a) J. T. Gallagher, J. E. Turnbull, Glycobiology 1992, 2, 523;
- (1992) Glycobiology , vol.2 , pp. 523
- Gallagher, J.T.¹ Turnbull, J.E.²

2
- 0028004630
- b) D. Spillmann, U. Lindahl, Curr. Opin. Struct. Biol. 1994, 4, 677;
- (1994) Curr. Opin. Struct. Biol. , vol.4 , pp. 677
- Spillmann, D.¹ Lindahl, U.²

3
- 0031023713
- c) K. S. Rostand, J. D. Esko, Infect. Immun. 1997, 65, 1;
- (1997) Infect. Immun. , vol.65 , pp. 1
- Rostand, K.S.¹ Esko, J.D.²

4
- 0001547769
- d) I. Capila, R. J. Linhardt, Angew. Chem. 2002, 114, 426;
- (2002) Angew. Chem. , vol.114 , pp. 426
- Capila, I.¹ Linhardt, R.J.²

5
- 0036469507
- Angew. Chem., Int. Ed. 2002, 41, 390;
- (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 390

6
- 0035997376
- e) J. D. Esko, S. B. Selleck, Annu. Rev. Biochem. 2002, 71, 435.
- (2002) Annu. Rev. Biochem. , vol.71 , pp. 435
- Esko, J.D.¹ Selleck, S.B.²

7
- 0001137548
- C. A. A. van Boeckel, M. Petitou, Angew. Chem. 1993, 105, 1741;
- (1993) Angew. Chem. , vol.105 , pp. 1741
- Van Boeckel, C.A.A.¹ Petitou, M.²

8
- 33748233635
- Angew. Chem., Int. Ed. 1993, 32, 1671;
- (1993) Angew. Chem., Int. Ed. , vol.32 , pp. 1671

9
- 33745889481
- M. Petitou, C. A. A. van Boeckel, Angew. Chem. 2004, 116, 3180;
- (2004) Angew. Chem. , vol.116 , pp. 3180
- Petitou, M.¹ Van Boeckel, C.A.A.²

10
- 4544280219
- Angew. Chem., Int. Ed. 2004, 43, 3118;
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3118

11
- 0041476049
- L. Poletti, L. Lay, Eur. J. Org. Chem. 2003, 2999;
- (2003) Eur. J. Org. Chem. , pp. 2999
- Poletti, L.¹ Lay, L.²

12
- 13344294985
- J. D. C. Codée, H. S. Overkleeft, G. A. van der Marel, C. A. A. van Boeckel, Drug Discov. Today: Technol. 2004, 1, 317.
- (2004) Drug Discov. Today: Technol. , vol.1 , pp. 317
- Codée, J.D.C.¹ Overkleeft, H.S.² Van Der Marel, G.A.³ Van Boeckel, C.A.A.⁴

13
- 2442549670
- A. K. Powell, E. A. Yates, D. G. Fernig, J. E. Turnbull, Glycobiology 2004, 14, 17R;
- (2004) Glycobiology , vol.14
- Powell, A.K.¹ Yates, E.A.² Fernig, D.G.³ Turnbull, J.E.⁴

14
- 0035984272
- D. L. Rabenstein, Nat. Prod. Rep. 2002, 19, 312.
- (2002) Nat. Prod. Rep. , vol.19 , pp. 312
- Rabenstein, D.L.¹

15
- 22644444072
- C. Noti, P. H. Seeberger, Chem. Biol. 2005, 12, 731.
- (2005) Chem. Biol. , vol.12 , pp. 731
- Noti, C.¹ Seeberger, P.H.²

16
- 0022384993
- J. T. Gallagher, A. Walker, Biochem. J. 1985, 230, 665.
- (1985) Biochem. J. , vol.230 , pp. 665
- Gallagher, J.T.¹ Walker, A.²

17
- 0032006297
- P. A. McBride, M. I. Wilson, P. Eikelenboom, A. Tunstall, M. E. Bruce, Exp. Neurol. 1998, 149, 447.
- (1998) Exp. Neurol. , vol.149 , pp. 447
- McBride, P.A.¹ Wilson, M.I.² Eikelenboom, P.³ Tunstall, A.⁴ Bruce, M.E.⁵

18
- 0020321767
- S. B. Prusiner, Science 1982, 216, 136.
- (1982) Science , vol.216 , pp. 136
- Prusiner, S.B.¹

19
- 0242650772
- Horizon Scientific Press, Wymondham, UK
- D. A. Harris, 'Prions. Molecular and Cellular Biology' Horizon Scientific Press, Wymondham, UK, 1999.
- (1999) Prions. Molecular and Cellular Biology
- Harris, D.A.¹

20
- 0035918180
- C. Leteux, W. Chai, K. Nagai, C. G. Herbert, A. M. Lawson, T. Feizi, J. Biol. Chem. 2001, 276, 12539.
- (2001) J. Biol. Chem. , vol.276 , pp. 12539
- Leteux, C.¹ Chai, W.² Nagai, K.³ Herbert, C.G.⁴ Lawson, A.M.⁵ Feizi, T.⁶

21
- 33845409771
- in press (DOI 10.1002/cbic.200600356)
- D. Hamza, R. Lucas, T. Feizi, W. Chai, D. Bonnaffé, A. Lubineau, ChemBioChem. 2006, 7, in press (DOI 10.1002/cbic.200600356).
- (2006) ChemBioChem. , vol.7
- Hamza, D.¹ Lucas, R.² Feizi, T.³ Chai, W.⁴ Bonnaffé, D.⁵ Lubineau, A.⁶

22
- 0028201330
- T. Feizi, M. S. Stoll, C.-T. Yuen, W. Chai, A. M. Lawson, Methods Enzymol. 1994, 230, 484.
- (1994) Methods Enzymol. , vol.230 , pp. 484
- Feizi, T.¹ Stoll, M.S.² Yuen, C.-T.³ Chai, W.⁴ Lawson, A.M.⁵

23
- 33845369109
- The Glycosciences Laboratory, Imperial College, personal communication
- T. Feizi, The Glycosciences Laboratory, Imperial College, personal communication.
- Feizi, T.¹

24
- 33746245828
- X. Liu, S. Siegrist, M. Amacker, R. Zurbriggen, G. Pluschke, P. H. Seeberger, ACS Chem. Biol. 2006, 1, 161.
- (2006) ACS Chem. Biol. , vol.1 , pp. 161
- Liu, X.¹ Siegrist, S.² Amacker, M.³ Zurbriggen, R.⁴ Pluschke, G.⁵ Seeberger, P.H.⁶

25
- 0037102205
- L. Schofield, M. C. Hewitt, K. Evans, M.-A. Siomos, P. H. Seeberger, Nature 2002, 418, 785.
- (2002) Nature , vol.418 , pp. 785
- Schofield, L.¹ Hewitt, M.C.² Evans, K.³ Siomos, M.-A.⁴ Seeberger, P.H.⁵

26
- 33845218763
- in press, DOI 10.1002/chem.200601103
- C. Noti, J. L. de Paz, L. Polito, P. H. Seeberger, Chem. - Eur. J., in press, DOI 10.1002/chem.200601103.
- Chem. - Eur. J.
- Noti, C.¹ De Paz, J.L.² Polito, L.³ Seeberger, P.H.⁴

27
- 0034465574
- M. Takatani, T. Nakama, K. Kubo, S. Manabe, Y. Nakahara, Y. Ito, Y. Nakahara, Glycoconj. J. 2000, 17, 361;
- (2000) Glycoconj. J. , vol.17 , pp. 361
- Takatani, M.¹ Nakama, T.² Kubo, K.³ Manabe, S.⁴ Nakahara, Y.⁵ Ito, Y.⁶ Nakahara, Y.⁷

28
- 0037415094
- H. A. Orgueira, A. Bartolozzi, P. Schell, R. E. J. N. Litjens, E. R. Palmacci, P. H. Seeberger, Chem. - Eur. J. 2003, 9, 140.
- (2003) Chem. - Eur. J. , vol.9 , pp. 140
- Orgueira, A.¹ Bartolozzi, A.² Schell, P.³ Litjens, R.E.J.N.⁴ Palmacci, E.R.⁵ Seeberger, P.H.⁶

29
- 0042320488
- P. Critchley, M. N. Willand, A. K. Rullay, D. H. G. Crout, Org. Biomol. Chem. 2003, 1, 928;
- (2003) Org. Biomol. Chem. , vol.1 , pp. 928
- Critchley, P.¹ Willand, M.N.² Rullay, A.K.³ Crout, D.H.G.⁴

30
- 0030739753
- N. Boden, R. J. Bushby, S. Clarkson, S. D. Evans, P. F. Knowles, A. Marsh, Tetrahedron 1997, 53, 10939.
- (1997) Tetrahedron , vol.53 , pp. 10939
- Boden, N.¹ Bushby, R.J.² Clarkson, S.³ Evans, S.D.⁴ Knowles, P.F.⁵ Marsh, A.⁶

31
- 3142777138
- L. J. van den Bos, J. D. C. Codée, J. C. van der Toorn, T. J. Boltje, J. H. van Boom, H. S. Overkleeft, G. A. van der Marel, Org. Lett. 2004, 6, 2165;
- (2004) Org. Lett. , vol.6 , pp. 2165
- Van Den Bos, L.J.¹ Codée, J.D.C.² Van Der Toorn, J.C.³ Boltje, T.J.⁴ Van Boom, J.H.⁵ Overkleeft, H.S.⁶ Van Der Marel, G.A.⁷

32
- 84860051581
- Ph.D. Thesis, Universiteit Leiden, NL-Leiden
- J. D. C. Codée, Ph.D. Thesis, Universiteit Leiden, NL-Leiden, 2004.
- (2004)
- Codée, J.D.C.¹

33
- 0035936861
- O. J. Plante, E. R. Palmacci, P. H. Seeberger, Science 2001, 291, 1523.
- (2001) Science , vol.291 , pp. 1523
- Plante, O.J.¹ Palmacci, E.R.² Seeberger, P.H.³

34
- 0033166819
- H. Yamada, M. Nakatani, T. Ikeda, Y. Marumoto, Tetrahedron Lett. 1999, 40, 5573;
- (1999) Tetrahedron Lett. , vol.40 , pp. 5573
- Yamada, H.¹ Nakatani, M.² Ikeda, T.³ Marumoto, Y.⁴

35
- 0034826966
- A. Bérces, G. Enright, T. Nukada, D. M. Whitfield, J. Am. Chem. Soc. 2001, 123, 5460;
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 5460
- Bérces, A.¹ Enright, G.² Nukada, T.³ Whitfield, D.M.⁴

36
- 0042671098
- A. Imamura, H. Ando, S. Korogi, G. Tanabe, O. Muraoka, H. Ishida, M. Kiso, Tetrahedron Lett. 2003, 44, 6725;
- (2003) Tetrahedron Lett. , vol.44 , pp. 6725
- Imamura, A.¹ Ando, H.² Korogi, S.³ Tanabe, G.⁴ Muraoka, O.⁵ Ishida, H.⁶ Kiso, M.⁷

37
- 33845364951
- personal communication
- S. Parsons, A. Proud, S. Flitsch, P. Wood, personal communication, 2004;
- (2004)
- Parsons, S.¹ Proud, A.² Flitsch, S.³ Wood, P.⁴

38
- 9644254286
- X. Guo, C. Cheng, X. Liu, X. Liu, R. Wang, D. Xie, L. Wang, Y. Zhao, J. Mol. Struct.: THEOCHEM 2004, 710, 201.
- (2004) J. Mol. Struct.: THEOCHEM , vol.710 , pp. 201
- Guo, X.¹ Cheng, C.² Liu, X.³ Liu, X.⁴ Wang, R.⁵ Xie, D.⁶ Wang, L.⁷ Zhao, Y.⁸

39
- 33646767009
- L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
- (1997) J. Appl. Crystallogr. , vol.30 , pp. 565
- Farrugia, L.J.¹

40
- 0035913760
- D. Crich, M. Smith, J. Am. Chem. Soc. 2001, 123, 9015;
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 9015
- Crich, D.¹ Smith, M.²

41
- 27844556493
- D. Crich, A. Banerjee, W. Li, Q. Yao, J. Carbohydr. Chem. 2005, 24, 415.
- (2005) J. Carbohydr. Chem. , vol.24 , pp. 415
- Crich, D.¹ Banerjee, A.² Li, W.³ Yao, Q.⁴

42
- 33845280670
- D. R. Mootoo, P. Konradsson, U. Udodong, B. Fraser-Reid, J. Am. Chem. Soc. 1988, 110, 5583;
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 5583
- Mootoo, D.R.¹ Konradsson, P.² Udodong, U.³ Fraser-Reid, B.⁴

43
- 85022498621
- B. Fraser-Reid, U. E. Udodong, Z. Wu, H. Ottosson, J. R. Merritt, C. S. Rao, C. Roberts, R. Madsen, Synlett 1992, 927.
- (1992) Synlett , pp. 927
- Fraser-Reid, B.¹ Udodong, U.E.² Wu, Z.³ Ottosson, H.⁴ Merritt, J.R.⁵ Rao, C.S.⁶ Roberts, C.⁷ Madsen, R.⁸

44
- 85047674602
- a) J. C. Castro-Palomino, R. R. Schmidt, Tetrahedron Lett. 1995, 36, 6871;
- (1995) Tetrahedron Lett. , vol.36 , pp. 6871
- Castro-Palomino, J.C.¹ Schmidt, R.R.²

45
- 0032492977
- b) A. V. Demchenko, G.-J. Boons, Tetrahedron Lett. 1998, 39, 3065;
- (1998) Tetrahedron Lett. , vol.39 , pp. 3065
- Demchenko, A.V.¹ Boons, G.-J.²

46
- 2942536229
- c) G. J. S. Lohman, P. H. Seeberger, J. Org. Chem. 2004, 69, 4081;
- (2004) J. Org. Chem. , vol.69 , pp. 4081
- Lohman, G.J.S.¹ Seeberger, P.H.²

47
- 0034835601
- d) D. Crich, V. Dudkin, J. Am. Chem. Soc. 2001, 123, 6819.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 6819
- Crich, D.¹ Dudkin, V.²

48
- 0000159086
- H. Paulsen, Angew. Chem. 1982, 94, 184;
- (1982) Angew. Chem. , vol.94 , pp. 184
- Paulsen, H.¹

49
- 0040657616
- Angew. Chem., Int. Ed. 1982, 21, 155.
- (1982) Angew. Chem., Int. Ed. , vol.21 , pp. 155

50
- 0018216477
- P. Sinaÿ, Pure Appl. Chem. 1978, 50, 1437;
- (1978) Pure Appl. Chem. , vol.50 , pp. 1437
- Sinaÿ, P.¹

51
- 0032844077
- A. Lubineau, D. Bonnaffé, Eur. J. Org. Chem. 1999, 2523.
- (1999) Eur. J. Org. Chem. , pp. 2523
- Lubineau, A.¹ Bonnaffé, D.²

52
- 4544361830
- R. Lucas, D. Hamza, A. Lubineau, D. Bonnaffé, Eur. J. Org. Chem. 2004, 2107.
- (2004) Eur. J. Org. Chem. , pp. 2107
- Lucas, R.¹ Hamza, D.² Lubineau, A.³ Bonnaffé, D.⁴

53
- 84980123865
- E. Fischer, Ber. Dtsch. Chem. Ges. 1914, 47, 1980;
- (1914) Ber. Dtsch. Chem. Ges. , vol.47 , pp. 1980
- Fischer, E.¹

54
- 17844384197
- L. F. Bornaghi, S.-A. Poulsen, Tetrahedron Lett. 2005, 46, 3485.
- (2005) Tetrahedron Lett. , vol.46 , pp. 3485
- Bornaghi, L.F.¹ Poulsen, S.-A.²

55
- 37049089831
- P. Szabó, J. Chem. Soc., Perkin Trans. 1 1989, 919.
- (1989) J. Chem. Soc., Perkin Trans. 1 , pp. 919
- Szabó, P.¹

56
- 0030701646
- N. Khiar, I. Alonso, N. Rodriguez, A. Fernandez-Mayoralas, J. Jimenez-Barbero, O. Nieto, F. Cano, C. Foces-Foces, M. Martin-Lomas, Tetrahedron Lett. 1997, 38, 8267;
- (1997) Tetrahedron Lett. , vol.38 , pp. 8267
- Khiar, N.¹ Alonso, I.² Rodriguez, N.³ Fernandez-Mayoralas, A.⁴ Jimenez-Barbero, J.⁵ Nieto, O.⁶ Cano, F.⁷ Foces-Foces, C.⁸ Martin-Lomas, M.⁹

57
- 0032556806
- D. Crich, J. Mataka, S. Sun, K.-C. Lam, A. L. Rheingold, D. J. Wink, Chem. Commun. 1998, 2763;
- (1998) Chem. Commun. , pp. 2763
- Crich, D.¹ Mataka, J.² Sun, S.³ Lam, K.-C.⁴ Rheingold, A.L.⁵ Wink, D.J.⁶

58
- 0033618521
- P. H. Buist, B. Behrouzian, K. D. MacIsaac, S. Cassel, P. Rollin, A. Imberty, C. Gautier, S. Pérez, P. Genix, Tetrahedron: Asymmetry 1999, 10, 2881;
- (1999) Tetrahedron: Asymmetry , vol.10 , pp. 2881
- Buist, P.H.¹ Behrouzian, B.² MacIsaac, K.D.³ Cassel, S.⁴ Rollin, P.⁵ Imberty, A.⁶ Gautier, C.⁷ Pérez, S.⁸ Genix, P.⁹

59
- 0037458995
- N. Khiar, I. Fernández, C. S. Araújo, J.-A. Rodríguez, B. Suárez, E. Álvarez, J. Org. Chem. 2003, 68, 1433.
- (2003) J. Org. Chem. , vol.68 , pp. 1433
- Khiar, N.¹ Fernández, I.² Araújo, C.S.³ Rodríguez, J.-A.⁴ Suárez, B.⁵ Álvarez, E.⁶

60
- 85011147512
- I. Shinkai, T. Liu, R. Reamer, M. Sletzinger, Synthesis 1980, 924.
- (1980) Synthesis , pp. 924
- Shinkai, I.¹ Liu, T.² Reamer, R.³ Sletzinger, M.⁴

61
- 0343550303
- T. Buskas, E. Söderberg, P. Konradsson, B. Fraser-Reid, J. Org. Chem. 2000, 65, 958;
- (2000) J. Org. Chem. , vol.65 , pp. 958
- Buskas, T.¹ Söderberg, E.² Konradsson, P.³ Fraser-Reid, B.⁴

62
- 33644946682
- J. L. de Paz, C. Noti, P. H. Seeberger, J. Am. Chem. Soc. 2006, 128, 2766.
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 2766
- De Paz, J.L.¹ Noti, C.² Seeberger, P.H.³

63
- 0015874433
- R. R. Traut, A. Bollen, T.-T. Sun, J. W. B. Hershey, J. Sundberg, L. R. Pierce, Biochemistry 1973, 12, 3266;
- (1973) Biochemistry , vol.12 , pp. 3266
- Traut, R.R.¹ Bollen, A.² Sun, T.-T.³ Hershey, J.W.B.⁴ Sundberg, J.⁵ Pierce, L.R.⁶

64
- 0018247303
- R. Jue, J. M. Lambert, L. R. Pierce, R. R. Traut, Biochemistry 1978, 17, 5399.
- (1978) Biochemistry , vol.17 , pp. 5399
- Jue, R.¹ Lambert, J.M.² Pierce, L.R.³ Traut, R.R.⁴

65
- 0004150157
- University of Göttingen, Göttingen
- G. M. Sheldrick, 'SHELXS-97 Program for the Solution of Crystal Structures', University of Göttingen, Göttingen, 1997.
- (1997) SHELXS-97 Program for the Solution of Crystal Structures
- Sheldrick, G.M.¹

66
- 0004150157
- University of Göttingen, Göttingen
- G. M. Sheldrick, 'SHELXL-97 Program for the Refinement of Crystal Structures', University of Göttingen, Göttingen, 1997.
- (1997) SHELXL-97 Program for the Refinement of Crystal Structures
- Sheldrick, G.M.¹

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.