Thiazolidine chemistry revisited: a fast, efficient and stable click-type reaction at physiological pH

被引:34
作者
Bermejo-Velasco, Daniel [1 ]
Nawale, Ganesh N. [1 ]
Oommen, Oommen P. [2 ,3 ]
Hilborn, Joens [1 ]
Varghese, Oommen P. [1 ]
机构
[1] Uppsala Univ, Translat Chem Biol Lab, Div Polymer Chem, Dept Chem Angstrom, Uppsala, Sweden
[2] Tampere Univ Technol, Bioengn & Nanomed Lab, Fac Biomed Sci & Engn, Tampere 33720, Finland
[3] BioMediTech Inst, Tampere 33720, Finland
关键词
N-TERMINAL CYSTEINE; COPPER(I)-CATALYZED AZIDE-ALKYNE; SITE-SPECIFIC CONJUGATION; IN-VIVO; PROTEIN MODIFICATION; CHEMICAL-SYNTHESIS; BUILDING-BLOCKS; PEPTIDE; LIGATION; BIOCONJUGATION;
D O I
10.1039/c8cc05405c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We describe the fast reaction kinetics between 1,2-aminothiols and aldehydes. Under physiological conditions such a click-type reaction afforded a thiazolidine product that remains stable and did not require any catalyst. This type of bioorthogonal reaction offers enormous potential for the coupling of biomolecules in an efficient and biocompatible manner.
引用
收藏
页码:12507 / 12510
页数:4
相关论文
共 43 条
  • [1] [Anonymous], 2008, ANGEW CHEM, DOI DOI 10.1002/ANGE.200802651
  • [2] Bandyopadhyay A, 2016, CHEM SCI, V7, P4589, DOI [10.1039/C6SC00172F, 10.1039/c6sc00172f]
  • [3] Kinetically controlled ligation for the convergent chemical synthesis of proteins
    Bang, Duhee
    Pentelute, Brad L.
    Kent, Stephen B. H.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) : 3985 - 3988
  • [4] Beatty KE, 2006, ANGEW CHEM, V118, P7524, DOI DOI 10.1002/ANGE.200602114
  • [5] Site-specific chemical modification of antibody fragments using traceless cleavable linkers
    Bernardes, Goncalo J. L.
    Steiner, Martina
    Hartmann, Isabelle
    Neri, Dario
    Casi, Giulio
    [J]. NATURE PROTOCOLS, 2013, 8 (11) : 2079 - 2089
  • [6] Genetic incorporation of 1,2-aminothiol functionality for site-specific protein modification via thiazolidine formation
    Bi, Xiaobao
    Pasunooti, Kalyan Kumar
    Tareq, Ahmad Hussen
    Takyi-Williams, John
    Liu, Chuan-Fa
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (23) : 5282 - 5285
  • [7] Cyclic peptides from linear unprotected peptide precursors through thiazolidine formation
    Botti, P
    Pallin, TD
    Tam, JP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (42) : 10018 - 10024
  • [8] Site-Specific Traceless Coupling of Potent Cytotoxic Drugs to Recombinant Antibodies for Pharmacodelivery
    Casi, Giulio
    Huguenin-Dezot, Nicolas
    Zuberbuehler, Kathrin
    Scheuermann, Joerg
    Neri, Dario
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (13) : 5887 - 5892
  • [9] A thiol probe for measuring unfolded protein load and proteostasis in cells
    Chen, Moore Z.
    Moily, Nagaraj S.
    Bridgford, Jessica L.
    Wood, Rebecca J.
    Radwan, Mona
    Smith, Trevor A.
    Song, Zhegang
    Tang, Ben Zhong
    Tilley, Leann
    Xu, Xiaohong
    Reid, Gavin E.
    Pouladi, Mahmoud A.
    Hong, Yuning
    Hatters, Danny M.
    [J]. NATURE COMMUNICATIONS, 2017, 8
  • [10] Second-generation difluorinated cyclooctynes for copper-free click chemistry
    Codelli, Julian A.
    Baskin, Jeremy M.
    Agard, Nicholas J.
    Berozzi, Carolyn R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (34) : 11486 - 11493