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Volumn 64, Issue 24, 1999, Pages 8948-8953

Preparation of a diglycosylated hydroxylysine building block used in solid-phase synthesis of a glycopeptide from type II collagen

Author keywords

[No Author keywords available]

Indexed keywords

COLLAGEN TYPE 2; GLYCOPEPTIDE; HYDROXYLYSINE;

EID: 0033607762     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990853d     Document Type: Note
Times cited : (44)

References (39)
  • 5
    • 0001100387 scopus 로고
    • Short glycopeptides in which hydroxylysine carried an α-D-Glc-(1→2)-β-D-Gal moiety have previously been prepared in solution (Koeners, H. J.; Schattenkerk, C.; Verhoeven, J. J.; van Boom, J. H. Tetrahedron 1981, 37, 1763-1771). However, this synthesis was less flexible because it involved glycosylation of hydroxylysine incorporated in a dipeptide. Moreover, the α- and ∈-amino groups of hydroxylysine carried identical protective groups, thereby preventing extension of the peptide at the N-terminus.
    • (1981) Tetrahedron , vol.37 , pp. 1763-1771
    • Koeners, H.J.1    Schattenkerk, C.2    Verhoeven, J.J.3    Van Boom, J.H.4
  • 6
    • 0002490637 scopus 로고
    • Lee, Y. C., Lee, R. T., Eds.; Academic Press: San Diego
    • Reviewed in (a) Meldal, M. In Neoglycoconjugates: Preparation and applications; Lee, Y. C., Lee, R. T., Eds.; Academic Press: San Diego, 1994; pp 145-198. (b) Arsequell, G.; Valencia, G. Tetrahedron: Asymmetry 1997, 8, 2839-2876. (c) Kihlberg, J.; Elofsson, M. Curr. Med. Chem. 1997, 4, 79-110.
    • (1994) Neoglycoconjugates: Preparation and Applications , pp. 145-198
    • Meldal, M.1
  • 7
    • 0030845782 scopus 로고    scopus 로고
    • Reviewed in (a) Meldal, M. In Neoglycoconjugates: Preparation and applications; Lee, Y. C., Lee, R. T., Eds.; Academic Press: San Diego, 1994; pp 145-198. (b) Arsequell, G.; Valencia, G. Tetrahedron: Asymmetry 1997, 8, 2839-2876. (c) Kihlberg, J.; Elofsson, M. Curr. Med. Chem. 1997, 4, 79-110.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 2839-2876
    • Arsequell, G.1    Valencia, G.2
  • 8
    • 0003060156 scopus 로고    scopus 로고
    • Reviewed in (a) Meldal, M. In Neoglycoconjugates: Preparation and applications; Lee, Y. C., Lee, R. T., Eds.; Academic Press: San Diego, 1994; pp 145-198. (b) Arsequell, G.; Valencia, G. Tetrahedron: Asymmetry 1997, 8, 2839-2876. (c) Kihlberg, J.; Elofsson, M. Curr. Med. Chem. 1997, 4, 79-110.
    • (1997) Curr. Med. Chem. , vol.4 , pp. 79-110
    • Kihlberg, J.1    Elofsson, M.2
  • 17
    • 0002503127 scopus 로고    scopus 로고
    • Kahn, S. H., O'Neill, R. A., Eds.; Harwood Academic Publishers: The Netherlands
    • Reviewed in (a) Norberg, T. In Modern Methods in Carbohydrate Synthesis; Kahn, S. H., O'Neill, R. A., Eds.; Harwood Academic Publishers: The Netherlands, 1996; pp 82-106. (b) Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179.
    • (1996) Modern Methods in Carbohydrate Synthesis , pp. 82-106
    • Norberg, T.1
  • 18
    • 37849189010 scopus 로고    scopus 로고
    • Reviewed in (a) Norberg, T. In Modern Methods in Carbohydrate Synthesis; Kahn, S. H., O'Neill, R. A., Eds.; Harwood Academic Publishers: The Netherlands, 1996; pp 82-106. (b) Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179.
    • (1997) Adv. Carbohydr. Chem. Biochem. , vol.52 , pp. 179
    • Garegg, P.J.1
  • 19
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    • note
    • Promotion was attempted by (a) N-odosuccinimide and silver trifluoromethanesulfonate, (b) N-iodosuccinimide and trifluoromethanesulfonic acid, (c) N-odosuccinimide and trimethylsilyl trifluoromethanesulfonate, (d) iodonium dicollidine trifluoromethanesulfonate, and (e) methylsulfenyl bromide and silver trifluoromethanesulfonate in the presence of 2,6-di-tert-butyl-4-methylpyridine.
  • 21
    • 0345646044 scopus 로고    scopus 로고
    • note
    • Promotion was attempted by (a) N-iodosuccinimide and silver trifluoromethanesulfonate, and (b) N-odosuccinimide and trifluoromethanesulfonic acid.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.