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Volumn 9, Issue 24, 2003, Pages 5997-6006

Oligosaccharide-Peptide Ligation of Glycosyl Thiolates with Dehydropeptides: Synthesis of S-Linked Mucin-Related Glycopeptide Conjugates

Author keywords

Carbohydrates; Chemoselective ligation; Dehydropeptide; Glycopeptides; Mucin

Indexed keywords

ANTIGENS; CARBOHYDRATES; ISOMERS; POLYSACCHARIDES; SYNTHESIS (CHEMICAL); TUMORS;

EID: 0346732163     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305290     Document Type: Article
Times cited : (67)

References (47)
  • 1
  • 4
    • 0036462604 scopus 로고    scopus 로고
    • d) B. G. Davis, Chem. Rev. 2002, 102, 579-601.
    • (2002) Chem. Rev. , vol.102 , pp. 579-601
    • Davis, B.G.1
  • 6
    • 0034599121 scopus 로고    scopus 로고
    • S.J. Danishefsky, J.R. Allen, Angew. Chem. 2000, 112, 882-911; Angew. Chem. Int. Ed. 2000, 39, 836-863.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 836-863
  • 8
    • 0035910559 scopus 로고    scopus 로고
    • a) S. Keil, C. Claus, W. Dippold, H. Kunz, Angew. Chem. 2001, 113, 379-382; Angew. Chem. Int. Ed. 2001, 40, 366-369;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 366-369
  • 10
    • 0035907720 scopus 로고    scopus 로고
    • b) N. Bezay, G. Dudziak, A. Liese, H. Kunz, Angew. Chem. 2001, 113, 2350-2353; Angew. Chem. Int. Ed. 2001, 40, 2292-2295;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2292-2295
  • 12
    • 0035887528 scopus 로고    scopus 로고
    • c) M. Rösch, H. Herzner, W. Dippold, M. Wild, D. Vestweber, H. Kunz, Angew. Chem. 2001, 113, 3954-3957; Angew. Chem. Int. Ed. 2001, 40, 3836-3839;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 3836-3839
  • 15
    • 0037468055 scopus 로고    scopus 로고
    • J. S. Miller, V. Y. Dudkin, G. J. Lyon, T. W. Muir, S. J. Danishefsky, Angew. Chem. 2003, 115, 447-450; Angew. Chem. Int. Ed. 2003, 42, 431-434.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 431-434
  • 16
    • 84980170811 scopus 로고
    • For approaches to the synthesis of the α-GalNHAc-Ser/Thr linkage, see, for example: a) H. Paulsen, W. Stenzel, Chem. Ber. 1978, 111, 2334-2347;
    • (1978) Chem. Ber. , vol.111 , pp. 2334-2347
    • Paulsen, H.1    Stenzel, W.2
  • 18
    • 0035898445 scopus 로고    scopus 로고
    • b) G. A. Winterfeld, R. R. Schmidt, Angew. Chem. 2001, 113, 2718-2721; Angew. Chem. Int. Ed. 2001, 40, 2654-2657.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2654-2657
  • 21
    • 0000953519 scopus 로고    scopus 로고
    • For other examples of chemical ligations via oxime linkers, see: a) S. E. Cervigni, P. Dumy, M. Mutter, Angew. Chem. 1996, 108, 1325-1328; Angew. Chem. Int. Ed. Engl. 1996, 35, 1230-1232;
    • (1996) Angew. Chem. , vol.108 , pp. 1325-1328
    • Cervigni, S.E.1    Dumy, P.2    Mutter, M.3
  • 22
    • 0029790914 scopus 로고    scopus 로고
    • For other examples of chemical ligations via oxime linkers, see: a) S. E. Cervigni, P. Dumy, M. Mutter, Angew. Chem. 1996, 108, 1325-1328; Angew. Chem. Int. Ed. Engl. 1996, 35, 1230-1232;
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1230-1232
  • 28
    • 33748219729 scopus 로고
    • b) M. Gerz, H. Matter, H. Kessler, Angew. Chem. 1993, 105, 311-313; Angew. Chem. Int. Ed. Engl. 1993, 32, 269-271;
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 269-271
  • 33
    • 0026928690 scopus 로고
    • and reference [1a]
    • For a related glycosylated STA peptide sequence in MUC1 see: P. L. Devine, I. F. C. McKenzie, BioEssays 1992, 14, 619-625, and reference [1a].
    • (1992) BioEssays , vol.14 , pp. 619-625
    • Devine, P.L.1    McKenzie, I.F.C.2
  • 43
    • 0347714863 scopus 로고    scopus 로고
    • note
    • The successful β-GalNHAc ligation complements our previous initial report of β-GlcNHAc ligations with monosaccharides (ref. [9]).
  • 44
    • 0035825787 scopus 로고    scopus 로고
    • For examples of the synthesis of C1-monosaccharide-amino acid/ dipeptide conjugates, see: a) S. B. Cohen, R. L. Halcomb, Org. Lett. 2001, 3, 405-407;
    • (2001) Org. Lett. , vol.3 , pp. 405-407
    • Cohen, S.B.1    Halcomb, R.L.2
  • 47
    • 0037662057 scopus 로고    scopus 로고
    • For the synthesis of β-thio mono- and disaccharide-peptide conjugates via the glycosylation of cysteine- and homocysteine-containing peptides with glycosyl halides, see: X. Zhu, K. Pachamuthu, R. R. Schmidt, J. Org. Chem. 2003, 68, 5641-5651.
    • (2003) J. Org. Chem. , vol.68 , pp. 5641-5651
    • Zhu, X.1    Pachamuthu, K.2    Schmidt, R.R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.