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Volumn 56, Issue 11, 2000, Pages 1579-1586

An improved synthesis of a galactosylated hydroxylysine building block and its use in solid-phase glycopeptide synthesis

Author keywords

Glycopeptides; Glycosylation; Solid phase synthesis

Indexed keywords

ALLYL COMPOUND; COLLAGEN TYPE 2; GALACTOSE; GLYCOPEPTIDE; HLA DR4 ANTIGEN; HYDROXYLYSINE; MAJOR HISTOCOMPATIBILITY ANTIGEN CLASS 2; SILICATE;

EID: 0034629259     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00061-2     Document Type: Article
Times cited : (43)

References (22)
  • 8
    • 0001100387 scopus 로고
    • A dipeptide building block in which hydroxylysine is carrying an α-D-Glc-(1→2)-β-D-Gal moiety has previously been prepared and used in the synthesis of short glycopeptides. However, as both the α- and ε-amino groups of hydroxylysine carry identical protective groups, selective extension of the peptide at the N-terminus cannot easily be achieved
    • A dipeptide building block in which hydroxylysine is carrying an α-D-Glc-(1→2)-β-D-Gal moiety has previously been prepared (Koeners, H. J. S. C.; Verhoeven, J. J.; van Boom, J.H. Tetrahedron 1981, 37, 1763-1771) and used in the synthesis of short glycopeptides. However, as both the α- and ε-amino groups of hydroxylysine carry identical protective groups, selective extension of the peptide at the N-terminus cannot easily be achieved.
    • (1981) Tetrahedron , vol.37 , pp. 1763-1771
    • Koeners, H.J.S.C.1    Verhoeven, J.J.2    Van Boom, J.H.3
  • 9
    • 0343311639 scopus 로고    scopus 로고
    • A more reproducible procedure for synthesis of 1 than reported in Ref. 4 has now been developed and is included in the experimental part
    • A more reproducible procedure for synthesis of 1 than reported in Ref. 4 has now been developed and is included in the experimental part.
  • 12
    • 0343747299 scopus 로고    scopus 로고
    • In a related study, various promoters and conditions were evaluated for glycosylation of hydroxylysine with 2,3,4-tri-O-acetyl-α-D-fucopyranosyl-bromide or thioglycoside derivatives. With exception of when silver silicate was used as promoter these attempts gave the target building block in low yields, often due to formation of orthoester side-products that could not be removed
    • In a related study, various promoters and conditions were evaluated for glycosylation of hydroxylysine with 2,3,4-tri-O-acetyl-α-D-fucopyranosyl-bromide or thioglycoside derivatives. With exception of when silver silicate was used as promoter these attempts gave the target building block in low yields, often due to formation of orthoester side-products that could not be removed.
  • 17
    • 0342442007 scopus 로고    scopus 로고
    • α-Fmoc group, was observed with MeOH and EtOH as co-solvents. A complete lack of reactivity even after 2 days was found in pure THF or EtOAc, when using iPrOH or nBuOH as co-solvents, or at elevated pressure (6 atmospheres in EtOAc)
    • α-Fmoc group, was observed with MeOH and EtOH as co-solvents. A complete lack of reactivity even after 2 days was found in pure THF or EtOAc, when using iPrOH or nBuOH as co-solvents, or at elevated pressure (6 atmospheres in EtOAc).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.