메뉴 건너뛰기




Volumn 6, Issue 8, 2000, Pages 1366-1375

A second generation synthesis of the MBr1 (globo-H) breast tumor antigen: New application of the n-pentenyl glycoside method for achieving complex carbohydrate protein linkages

Author keywords

Antigens; Carbohydrates; Glycoconjugates; Glycosides; Immunology

Indexed keywords

CANCER VACCINE; CARBOHYDRATE DERIVATIVE; CARRIER PROTEIN; GLYCOCONJUGATE; GLYCOSIDE; MBR 1 ANTIGEN; TUMOR ANTIGEN; TUMOR VACCINE; UNCLASSIFIED DRUG;

EID: 0034646882     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(20000417)6:8<1366::aid-chem1366>3.3.co;2-b     Document Type: Article
Times cited : (72)

References (105)
  • 43
    • 0000477769 scopus 로고    scopus 로고
    • For a review on efforts from our laboratory see S. J. Danishefsky, J. R. Allen, Angew. Chem. 2000, 112, 882; Angew. Chem. Int. Ed. 2000, 39, 836.
    • (2000) Angew. Chem. , vol.112 , pp. 882
    • Danishefsky, S.J.1    Allen, J.R.2
  • 44
    • 0034599121 scopus 로고    scopus 로고
    • For a review on efforts from our laboratory see S. J. Danishefsky, J. R. Allen, Angew. Chem. 2000, 112, 882; Angew. Chem. Int. Ed. 2000, 39, 836.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 836
  • 45
  • 46
    • 0023768505 scopus 로고
    • 3 which contains the ABC trisaccharide domain see K. C. Nicolaou, T. Caulifield, H. Kataoka, T. Kumazawa, J. Am. Chem. Soc. 1988, 110, 7910. For the synthesis of ABCDE pentasaccharide moiety see (a) S. Nunomura, T. Ogawa, Tetrahedron Lett. 1988, 29, 5681 b) T. K. Park, I. J. Kim, S. J. Danishefsky, Tetrahedron Lett. 1995, 36, 9089.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 7910
    • Nicolaou, K.C.1    Caulifield, T.2    Kataoka, H.3    Kumazawa, T.4
  • 47
    • 0023756294 scopus 로고
    • 3 which contains the ABC trisaccharide domain see K. C. Nicolaou, T. Caulifield, H. Kataoka, T. Kumazawa, J. Am. Chem. Soc. 1988, 110, 7910. For the synthesis of ABCDE pentasaccharide moiety see (a) S. Nunomura, T. Ogawa, Tetrahedron Lett. 1988, 29, 5681 b) T. K. Park, I. J. Kim, S. J. Danishefsky, Tetrahedron Lett. 1995, 36, 9089.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 5681
    • Nunomura, S.1    Ogawa, T.2
  • 48
    • 0028791701 scopus 로고
    • 3 which contains the ABC trisaccharide domain see K. C. Nicolaou, T. Caulifield, H. Kataoka, T. Kumazawa, J. Am. Chem. Soc. 1988, 110, 7910. For the synthesis of ABCDE pentasaccharide moiety see (a) S. Nunomura, T. Ogawa, Tetrahedron Lett. 1988, 29, 5681 b) T. K. Park, I. J. Kim, S. J. Danishefsky, Tetrahedron Lett. 1995, 36, 9089.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 9089
    • Park, T.K.1    Kim, I.J.2    Danishefsky, S.J.3
  • 50
    • 0030803409 scopus 로고    scopus 로고
    • a) G. Ragupathi, T. K. Park, S. Zhang, I. J. Kim, L. Graber, S. Adluri, K. O. Lloyd, S. J. Danihefsky, P. O. Livingston, Angew. Chem. 1997. 109, 66; Angew. Chem. Int. Ed. Engl. 1997, 36, 125
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 125
  • 52
    • 0033558181 scopus 로고    scopus 로고
    • b) G. Ragupathi, S. F. Slovin, S. Adluri, D. Sames, I. J. Kim, H. Kim, M. Spassova, W. G. Bornmann, K. O. Lloyd, H. I. Scher, P. O. Livingston, S. J. Danishefsky. Angew. Chem. 1999, 111, 590; Angew. Chem. Int. Ed. 1999, 38, 563
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 563
  • 58
    • 0029739240 scopus 로고    scopus 로고
    • S. J. Danishefsky, M. T. Bilodeau, Angew. Chem. 1996, 108, 1482: Angew. Chem. Int. Ed. Engl. 1996, 35, 1380.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1380
  • 63
    • 85088005107 scopus 로고    scopus 로고
    • note
    • y, the antigen KH-1, and the N3 antigens using this general method. See reference [12] for a review of this methodology as applied to carbohydrate-based vaccines.
  • 73
    • 33845278486 scopus 로고    scopus 로고
    • Benzylidine formation through the C4′-C6′ hydroxyl groups on unprotected lactosides have been reported. See a) K. Jansson, S. Ahlfors, T. Frejd, J. Kihlberg, G. Mangusson, J. Org. Chem. 1998, 53, 5629 b) F. Koeman, J. P. Kamerling, J. F. G. Vliegenthart, Tetrahedron 1993, 49, 5291 c) D. Qiu, R. R. Schmidt, Liebigs Ann. 1992, 217.
    • (1998) J. Org. Chem. , vol.53 , pp. 5629
    • Jansson, K.1    Ahlfors, S.2    Frejd, T.3    Kihlberg, J.4    Mangusson, G.5
  • 74
    • 0027238866 scopus 로고
    • Benzylidine formation through the C4′-C6′ hydroxyl groups on unprotected lactosides have been reported. See a) K. Jansson, S. Ahlfors, T. Frejd, J. Kihlberg, G. Mangusson, J. Org. Chem. 1998, 53, 5629 b) F. Koeman, J. P. Kamerling, J. F. G. Vliegenthart, Tetrahedron 1993, 49, 5291 c) D. Qiu, R. R. Schmidt, Liebigs Ann. 1992, 217.
    • (1993) Tetrahedron , vol.49 , pp. 5291
    • Koeman, F.1    Kamerling, J.P.2    Vliegenthart, J.F.G.3
  • 75
    • 84986695073 scopus 로고
    • Benzylidine formation through the C4′-C6′ hydroxyl groups on unprotected lactosides have been reported. See a) K. Jansson, S. Ahlfors, T. Frejd, J. Kihlberg, G. Mangusson, J. Org. Chem. 1998, 53, 5629 b) F. Koeman, J. P. Kamerling, J. F. G. Vliegenthart, Tetrahedron 1993, 49, 5291 c) D. Qiu, R. R. Schmidt, Liebigs Ann. 1992, 217.
    • (1992) Liebigs Ann. , pp. 217
    • Qiu, D.1    Schmidt, R.R.2
  • 89
    • 7744237974 scopus 로고    scopus 로고
    • note
    • The protein to carbohydrate ratio obtained from the reductive amination with KLH using pentenyl glycoside 1c is comparable to the corresponding reaction using allyl giycoside 1b.
  • 103
    • 7744242191 scopus 로고    scopus 로고
    • note
    • We also observed a small amount of the anomeric N-acetamido compound in this reaction. See reference [20] for applications of this chemistry.
  • 105
    • 0033485771 scopus 로고    scopus 로고
    • We also have an interest in the tumor antigen fucosyl GM1. The corresponding pentenyl glycoside has similarly been synthesized and effectively coupled to carrier protein KLH. See J. R. Allen, G. Ragupathi, P. O. Livingston, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 10875.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 10875
    • Allen, J.R.1    Ragupathi, G.2    Livingston, P.O.3    Danishefsky, S.J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.