Solid-phase synthesis of oligourea peptidomimetics employing the Fmoc protection strategy

被引：74
|
作者：
Boeijen, A [1 ]
van Ameijde, J [1 ]
Liskamp, RMJ [1 ]
机构：
[1] Univ Utrecht, Dept Med Chem, Inst Pharmaceut Sci, NL-3508 TB Utrecht, Netherlands
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 25期
关键词：
D O I：
10.1021/jo010656q
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A solid-phase-Fmoc-based-synthesis strategy is described for oligourea peptidomimetics as well as a convenient general synthesis approach for the preparation of the required building blocks 5a-j and 5k. These are suitable for use in peptide or robot synthesizers, which is illustrated by the synthesis of oligourea peptidomimetics of part of Leu-enkephalin (10) and a neurotensin derivative (17).
引用
收藏
页码：8454 / 8462
页数：9
相关论文
共 50 条
  • [1] Solid-phase synthesis of oligourea peptidomimetics
    Boeijen, A
    Liskamp, RMJ
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (09) : 2127 - 2135
  • [2] AN EFFICIENT PROCEDURE FOR SOLID-PHASE SYNTHESIS OF PHOSPHOPEPTIDES BY THE FMOC STRATEGY
    WAKAMIYA, T
    SARUTA, K
    YASUOKA, J
    KUSUMOTO, S
    CHEMISTRY LETTERS, 1994, (06) : 1099 - 1102
  • [3] Solid-phase synthesis of sulfamate peptidomimetics
    Farrera-Sinfreu, Josep
    Albericio, Fernando
    Royo, Miriam
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2007, 9 (03): : 501 - 506
  • [4] The Fmoc-Strategy Solid-Phase Synthesis of O-Phosphopeptide
    Chen Shui-Bing
    Li Yan-Mei
    Zhao Gang
    Luo Shi-Zhong
    Zhao Yu-Fen
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2001, 22 : 106 - 110
  • [5] A Submonomer Solid-Phase Synthesis Strategy of Bio-Active Peptidomimetics
    Sabatino, David
    BIOPOLYMERS, 2011, 96 (04) : 463 - 463
  • [6] Advances in Fmoc solid-phase peptide synthesis
    Behrendt, Raymond
    White, Peter
    Offer, John
    JOURNAL OF PEPTIDE SCIENCE, 2016, 22 (01) : 4 - 27
  • [7] Alternative to piperidine in Fmoc solid-phase synthesis
    Hachmann, J
    Lebl, M
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2006, 8 (02): : 149 - 149
  • [8] Toward sustainable solid-phase peptide synthesis strategy - in situ Fmoc removal
    Mthethwa, Ndumiso
    Nandhini, K. P.
    Kumar, Ashish
    Sharma, Anamika
    de la Torre, Beatriz G.
    Albericio, Fernando
    GREEN CHEMISTRY LETTERS AND REVIEWS, 2024, 17 (01)
  • [9] Nsc and Fmoc Nα-amino protection for solid-phase peptide synthesis:: a parallel study
    Carreño, C
    Méndez, ME
    Kim, YD
    Kim, HJ
    Kates, SA
    Andreu, D
    Albericio, F
    JOURNAL OF PEPTIDE RESEARCH, 2000, 56 (02): : 63 - 69
  • [10] Protection of 3,4-dihydroxyphenylalanine (DOPA) for Fmoc solid-phase peptide synthesis
    Hu, BH
    Messersmith, PB
    TETRAHEDRON LETTERS, 2000, 41 (31) : 5795 - 5798
12345