Synthesis of biotinylated glycosulfopeptides by chemoselective ligation

被引:13
作者
Durieux, P [1 ]
Fernandez-Carneado, J [1 ]
Tuchscherer, G [1 ]
机构
[1] Univ Lausanne, Inst Organ Chem, CH-1015 Lausanne, Switzerland
关键词
peptide conjugates; biotinylated glycosulfopeptides; chemoselective ligation; PSGL-1; mimetics;
D O I
10.1016/S0040-4039(01)00167-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tyrosine sulfation and O-glycosylation are two post-translational modifications playing an essential rule in modulation of biological activity, protein folding and cellular communication. Here, a novel chemical approach for the synthesis of biotinylated glycosulfopeptides is described based on a combination of acid labile protecting groups, highly acid sensitive resins and two orthogonal chemoselective ligation reactions. (C) 2001 Published by Elsevier Science Ltd.
引用
收藏
页码:2297 / 2299
页数:3
相关论文
共 22 条
  • [1] Synthesis of glycopeptides and lipopeptides by chemoselective ligation
    Cervigni, SE
    Dumy, P
    Mutter, M
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (11): : 1230 - 1232
  • [2] A highly convergent total synthetic route to glycopeptides carrying a high-mannose core pentasaccharide domain N-linked to a natural peptide motif
    Danishefsky, SJ
    Hu, S
    Cirillo, PF
    Eckhardt, M
    Seeberger, PH
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (10) : 1617 - 1628
  • [3] CONVENIENT TOTAL SYNTHESIS OF A 4-HELIX TASP MOLECULE BY CHEMOSELECTIVE LIGATION
    DAWSON, PE
    KENT, SBH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (16) : 7263 - 7266
  • [4] Glycobiology: Toward understanding the function of sugars
    Dwek, RA
    [J]. CHEMICAL REVIEWS, 1996, 96 (02) : 683 - 720
  • [5] A novel glycosulfopeptide binds to P-selectin and inhibits leukocyte adhesion to P-selectin
    Leppänen, A
    Mehta, P
    Ouyang, YB
    Ju, TZ
    Helin, J
    Moore, KL
    van Die, I
    Canfield, WM
    McEver, RP
    Cummings, RD
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 1999, 274 (35) : 24838 - 24848
  • [6] Identification of N-terminal residues on P-selectin glycoprotein ligand-1 required for binding to P-selectin
    Liu, W
    Ramachandran, V
    Kang, J
    Kishimoto, TK
    Cummings, RD
    McEver, RP
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 1998, 273 (12) : 7078 - 7087
  • [7] Marcaurelle LA, 1999, CHEM-EUR J, V5, P1384, DOI 10.1002/(SICI)1521-3765(19990503)5:5<1384::AID-CHEM1384>3.3.CO
  • [8] 2-O
  • [9] Selectin-carbohydrate interactions during inflammation and metastasis
    McEver, RP
    [J]. GLYCOCONJUGATE JOURNAL, 1997, 14 (05) : 585 - 591
  • [10] MELDAL M, 1997, CURR OPIN CHEM BIOL, V1, P5520