Solid phase synthesis of C-terminal carbohydrate modified enkephalins

被引:42
作者
Drouillat, B [1 ]
Kellam, B [1 ]
Dekany, G [1 ]
Starr, MS [1 ]
Toth, I [1 ]
机构
[1] UNIV LONDON,SCH PHARM,DEPT PHARMACEUT & BIOL CHEM,LONDON WC1N 1AX,ENGLAND
基金
英国惠康基金;
关键词
D O I
10.1016/S0960-894X(97)00395-8
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
1-Azido-2,3,4-tri-O-acetyl-beta-D-glucuronic acid (1), immobilised on 2-chlorotrityl and NovaSyn TGR resin, was efficiently reduced to its corresponding resin bound glycosyl amine (3) using propane-1,3-dithiol and triethylamine. Subsequent acylation of (3) with (1), generated the carbohydrate dimer (4). In addition, Fmoc based peptide syntheses performed on (3) and (4) afforded the C-terminal modified Leu and Met-enkephalins (7-10). Preliminary pharmacological evaluation of these compounds identified glycopeptide (7) as a potent and selective delta-opioid receptor agonist. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:2247 / 2250
页数:4
相关论文
共 26 条
  • [1] Solid phase synthesis of oligosaccharides
    Adinolfi, M
    Barone, G
    DeNapoli, L
    Iadonisi, A
    Piccialli, G
    [J]. TETRAHEDRON LETTERS, 1996, 37 (28) : 5007 - 5010
  • [2] Balkenhohl F, 1996, ANGEW CHEM INT EDIT, V35, P2289
  • [3] BAYLEY H, 1978, TETRAHEDRON LETT, V19, P3633
  • [4] BELL GI, 1993, J BIOL CHEM, V268, P19161
  • [5] POLYMER-SUPPORTED SOLUTION SYNTHESIS OF OLIGOSACCHARIDES USING A NOVEL VERSATILE LINKER FOR THE SYNTHESIS OF D-MANNOPENTAOSE, A STRUCTURAL UNIT OF D-MANNANS OF PATHOGENIC YEASTS
    DOUGLAS, SP
    WHITFIELD, DM
    KREPINSKY, JJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (07) : 2116 - 2117
  • [6] FRECHET JM, 1971, J AM CHEM SOC, V93, P492
  • [7] GUTHRIE RD, 1973, J CHEM SOC P1, V1, P2441
  • [8] SYNTHESIS, STRUCTURE AND REACTIONS OF GLYCOSYL AZIDES
    GYORGYDEAK, Z
    SZILAGYI, L
    PAULSEN, H
    [J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1993, 12 (02) : 139 - 163
  • [9] HANCOCK WS, 1976, ANAL BIOCHEM, V71, P260, DOI 10.1016/0003-2697(76)90034-8
  • [10] Solid-phase organic reactions: A review of the recent literature
    Hermkens, PHH
    Ottenheijm, HCJ
    Rees, D
    [J]. TETRAHEDRON, 1996, 52 (13) : 4527 - 4554