An improved deblocking agent for direct Fmoc solid-phase synthesis of peptide thioesters

被引:31
|
作者
Bu, XZ
Xie, GY
Law, CW
Guo, ZH [1 ]
机构
[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China
[2] Hong Kong Univ Sci & Technol, Biotechnol Res Ctr, Kowloon, Hong Kong, Peoples R China
关键词
D O I
10.1016/S0040-4039(02)00237-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
To synthesize peptide thioesters directly on a solid support for use as substrate analogues for thioesterases in non-ribosomal peptide synthases, we modified a reagent compatible with Fmoc solid-phase peptide synthesis that efficiently removes the protecting group while keeping the thioester intact. The deprotecting reagent, consisting of DBU and HOBt, was successfully used to prepare a decapeptide in high yield. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2419 / 2422
页数:4
相关论文
共 50 条
  • [1] Direct preparation of peptide thioesters using an Fmoc solid-phase method
    Li, XQ
    Kawakami, T
    Aimoto, S
    TETRAHEDRON LETTERS, 1998, 39 (47) : 8669 - 8672
  • [2] 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
  • [3] Preparation of Peptide Thioesters through Fmoc-Based Solid-Phase Peptide Synthesis by Using Amino Thioesters
    Stuhr-Hansen, Nicolai
    Wilbek, Theis S.
    Stromgaard, Kristian
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (24) : 5290 - 5294
  • [4] Direct Fmoc-Chemistry-Based Solid-Phase Synthesis of Peptidyl Thioesters
    Sharma, Indrajeet
    Crich, David
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (16) : 6518 - 6524
  • [5] Fmoc-compatible solid-phase peptide synthesis of long C-terminal peptide thioesters
    Sewing, A
    Hilvert, D
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (18) : 3395 - +
  • [6] Facile, Fmoc-compatible solid-phase synthesis of peptide C-terminal thioesters
    Swinnen, D
    Hilvert, D
    ORGANIC LETTERS, 2000, 2 (16) : 2439 - 2442
  • [7] 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
  • [8] Advances in Fmoc solid-phase peptide synthesis
    Behrendt, Raymond
    White, Peter
    Offer, John
    JOURNAL OF PEPTIDE SCIENCE, 2016, 22 (01) : 4 - 27
  • [9] Fmoc solid-phase synthesis of C-terminal peptide thioesters by formation of a pyroglutamyl imide moiety
    Tofteng, A. Pernille
    Conde-Frieboes, Kilian W.
    Hoeg-Jensen, Thomas
    Jensen, Knud J.
    JOURNAL OF PEPTIDE SCIENCE, 2008, 14 (08) : 15 - 15
  • [10] A new Fmoc-compatible method for the solid-phase synthesis of peptide C-terminal α-thioesters
    Camarero, JA
    de Yoreo, J
    Mitchell, AR
    BIOPOLYMERS, 2003, 71 (03) : 363 - 363