Advances in Fmoc solid-phase peptide synthesis

被引:484
|
作者
Behrendt, Raymond [2 ]
White, Peter [3 ]
Offer, John [1 ]
机构
[1] Francis Crick Inst, 215 Euston Rd, London NW1 2BE, England
[2] Merck & Cie, Novabiochem, Laternenacker 5, CH-8200 Schaffhausen, Switzerland
[3] Merck Chem Ltd, Novabiochem, Beeston NG9 2JR, England
基金
英国医学研究理事会;
关键词
solid-phase peptide synthesis; Fmoc; tBu; aspartimide; peptide thioester; post-translational modification; protecting group; racemisation; NATIVE CHEMICAL LIGATION; BOND-CONTAINING-POLYPEPTIDES; LABILE PROTECTING GROUPS; ACYL SHIFT REACTION; N-ALPHA-FMOC; ASPARTIMIDE FORMATION; SIDE REACTIONS; AMINO-ACIDS; TYROSINE SULFATION; EFFICIENT SYNTHESIS;
D O I
10.1002/psc.2836
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Today, Fmoc SPPS is the method of choice for peptide synthesis. Very-high-quality Fmoc building blocks are available at low cost because of the economies of scale arising from current multiton production of therapeutic peptides by Fmoc SPPS. Many modified derivatives are commercially available as Fmoc building blocks, making synthetic access to a broad range of peptide derivatives straightforward. The number of synthetic peptides entering clinical trials has grown continuously over the last decade, and recent advances in the Fmoc SPPS technology are a response to the growing demand from medicinal chemistry and pharmacology. Improvements are being continually reported for peptide quality, synthesis time and novel synthetic targets. Topical peptide research has contributed to a continuous improvement and expansion of Fmoc SPPS applications. Copyright (c) 2015 European Peptide Society and John Wiley & Sons, Ltd.
引用
下载
收藏
页码:4 / 27
页数:24
相关论文
共 50 条
  • [1] Greening Fmoc/tBu solid-phase peptide synthesis
    Al Musaimi, Othman
    de la Torre, Beatriz G.
    Albericio, Fernando
    GREEN CHEMISTRY, 2020, 22 (04) : 996 - 1018
  • [2] Boosting Fmoc Solid-Phase Peptide Synthesis by Ultrasonication
    Merlino, Francesco
    Tomassi, Stefano
    Yousif, Ali M.
    Messere, Anna
    Marinelli, Luciana
    Grieco, Paolo
    Novellino, Ettore
    Cosconati, Sandro
    Di Maro, Salvatore
    ORGANIC LETTERS, 2019, 21 (16) : 6378 - 6382
  • [3] ASPARAGINE COUPLING IN FMOC SOLID-PHASE PEPTIDE-SYNTHESIS
    GAUSEPOHL, H
    KRAFT, M
    FRANK, RW
    INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1989, 34 (04): : 287 - 294
  • [4] SOLID-PHASE SYNTHESIS OF A CYCLIC PEPTIDE USING FMOC CHEMISTRY
    MCMURRAY, JS
    TETRAHEDRON LETTERS, 1991, 32 (52) : 7679 - 7682
  • [5] Fast conventional Fmoc solid-phase peptide synthesis with HCTU
    Hood, Christina A.
    Fuentes, German
    Patel, Hirendra
    Page, Karen
    Menakuru, Mahendra
    Park, Jae H.
    JOURNAL OF PEPTIDE SCIENCE, 2008, 14 (01) : 97 - 101
  • [6] Synthesis of suitably protected γ-hydroxyvaline for use in fmoc solid-phase peptide synthesis
    Cudic, M.
    Mari, F.
    Fields, G. B.
    BIOPOLYMERS, 2007, 88 (04) : 574 - 574
  • [7] 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
  • [8] 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
  • [9] 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)
  • [10] 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