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
  • [41] Automated solid-phase synthesis of metabolically stabilized triazolo-peptidomimetics
    Guarrochena, Xabier
    Kaudela, Barbara
    Mindt, Thomas L.
    JOURNAL OF PEPTIDE SCIENCE, 2023, 29 (09)
  • [42] Fmoc solid-phase synthesis of peptide thioesters by masking as trithioortho esters
    Brask, J
    Albericio, F
    Jensen, KJ
    ORGANIC LETTERS, 2003, 5 (16) : 2951 - 2953
  • [43] In situ Fmoc removal - a sustainable solid-phase peptide synthesis approach
    Kumar, Ashish
    Sharma, Anamika
    de la Torre, Beatriz G.
    Albericio, Fernando
    GREEN CHEMISTRY, 2022, 24 (12) : 4887 - 4896
  • [44] Morpholine, a strong contender for Fmoc removal in solid-phase peptide synthesis
    Mthembu, Sinenhlanhla N.
    Chakraborty, Amit
    Schonleber, Ralph
    Albericio, Fernando
    de la Torre, Beatriz G.
    JOURNAL OF PEPTIDE SCIENCE, 2024, 30 (02)
  • [45] DEPROTECTION OF FLUORENYLMETHYLOXYCARBONYL (FMOC) GROUP IN SOLID-PHASE PEPTIDE-SYNTHESIS
    RAMPAL, JB
    FASEB JOURNAL, 1988, 2 (05): : A1542 - A1542
  • [46] Improved Fmoc Solid-Phase Peptide Synthesis of Oxytocin with High Bioactivity
    Sun, Pengcheng
    Tang, Wenli
    Huang, Yu
    Hu, Bi-Huang
    SYNLETT, 2017, 28 (14) : 1780 - 1784
  • [47] Leveraging Hydrazide as Protection for Carboxylic Acid: Suppression of Aspartimide Formation during Fmoc Solid-Phase Peptide Synthesis
    Sato, Kohei
    Uemura, Haruna
    Narumi, Tetsuo
    Mase, Nobuyuki
    ORGANIC LETTERS, 2024, 26 (21) : 4497 - 4501
  • [48] Solid phase synthesis of peptidomimetics
    Mayer, JP
    Bankaitis-Davis, D
    Beaton, G
    Bjergarde, K
    Gaudino, JJ
    Goodman, BA
    Herrera, CJ
    Lenz, DM
    Lewis, GS
    Tarlton, CM
    Zhang, J
    PEPTIDES: FRONTIERS OF PEPTIDES SCIENCE, 1999, : 31 - 33
  • [49] FMOC SOLID-PHASE SYNTHESIS OF TYR(P)-CONTAINING PEPTIDES THROUGH TERT-BUTYL PHOSPHATE PROTECTION
    PERICH, JW
    REYNOLDS, EC
    INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1991, 37 (06): : 572 - 575
  • [50] AN ACID-LABILE LINKER FOR SOLID-PHASE OLIGORIBONUCLEOTIDE SYNTHESIS USING FMOC GROUP FOR 5'-HYDROXYL PROTECTION
    PALOM, Y
    ALAZZOUZI, E
    GORDILLO, F
    GRANDAS, A
    PEDROSO, E
    TETRAHEDRON LETTERS, 1993, 34 (13) : 2195 - 2198
12345