Photoredox-Catalyzed Labeling of Hydroxyindoles with Chemoselectivity (PhotoCLIC) for Site-Specific Protein Bioconjugation

被引：9
|
作者：
Roy, Soumya Jyoti Singha [1 ]
Loynd, Conor [1 ]
Jewel, Delilah [1 ]
Canarelli, Sarah E. [1 ]
Ficaretta, Elise D. [1 ]
Pham, Quan A. [1 ]
Weerapana, Eranthie [1 ]
Chatterjee, Abhishek [1 ]
机构：
[1] Boston Coll, Dept Chem, 2609 Beacon St, Chestnut Hill, MA 02467 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 27期
关键词：
Bioconjugation; Chemoselectivity; Photoredox Catalysis; Protein Labeling; AMINO-ACID MUTAGENESIS; CLICK CHEMISTRY; GENETIC-CODE; 5-HYDROXYTRYPTOPHAN; FUNCTIONALIZATION; RESIDUES; PLATFORM; OXYGEN; CELLS;
D O I：
10.1002/anie.202300961
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We have developed a novel visible-light-catalyzed bioconjugation reaction, PhotoCLIC, that enables chemoselective attachment of diverse aromatic amine reagents onto a site-specifically installed 5-hydroxytryptophan residue (5HTP) on full-length proteins of varied complexity. The reaction uses catalytic amounts of methylene blue and blue/red light-emitting diodes (455/650 nm) for rapid site-specific protein bioconjugation. Characterization of the PhotoCLIC product reveals a unique structure formed likely through a singlet oxygen-dependent modification of 5HTP. PhotoCLIC has a wide substrate scope and its compatibility with strain-promoted azide-alkyne click reaction, enables site-specific dual-labeling of a target protein.
引用
收藏
页数：7
相关论文
共 50 条
  • [41] A Versatile Approach for the Site-Specific Modification of Recombinant Antibodies Using a Combination of Enzyme-Mediated Bioconjugation and Click Chemistry
    Alt, Karen
    Paterson, Brett M.
    Westein, Erik
    Rudd, Stacey E.
    Poniger, Stan S.
    Jagdale, Shweta
    Ardipradja, Katie
    Connell, Timothy U.
    Krippner, Guy Y.
    Nair, Ashish K. N.
    Wang, Xiaowei
    Tochon-Danguy, Henri J.
    Donnelly, Paul S.
    Peter, Karlheinz
    Hagemeyer, Christoph E.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (26) : 7515 - 7519
  • [42] A Platform for Site-Specific DNA-Antibody Bioconjugation by Using Benzoylacrylic-Labelled Oligonucleotides
    Konc, Juraj
    Brown, Libby
    Whiten, Daniel R.
    Zuo, Yukun
    Ravn, Peter
    Klenerman, David
    Bernardes, Goncalo J. L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (49) : 25905 - 25913
  • [43] Bioorthogonal site-specific labeling of the 5′-cap structure in eukaryotic mRNAs
    Holstein, Josephin Marie
    Schulz, Daniela
    Rentmeister, Andrea
    CHEMICAL COMMUNICATIONS, 2014, 50 (34) : 4478 - 4481
  • [44] Design of multivalent fluorescent dendritic probes for site-specific labeling of biomolecules
    Martin-Serrano Ortiz, Angela
    Stenstrom, Patrik
    Antunez, Pablo Mesa
    Andren, Oliver C. J.
    Torres, Maria J.
    Montanez, Maria I.
    Malkoch, Michael
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2018, 56 (15) : 1609 - 1616
  • [45] Site-Specific Incorporation of Two ncAAs for Two-Color Bioorthogonal Labeling and Crosslinking of Proteins on Live Mammalian Cells
    Meineke, Birthe
    Heimgertner, Johannes
    Eirich, Juergen
    Landreh, Michael
    Elsasser, Simon J.
    CELL REPORTS, 2020, 31 (12):
  • [46] Multiple Site-Specific in Vitro Labeling of Single-Chain Antibody
    Ramakrishnan, Boopathy
    Boeggeman, Elizabeth
    Manzoni, Maria
    Zhu, Zhongyu
    Loomis, Kristin
    Puri, Anu
    Dimitrov, Dimiter S.
    Qasba, Pradman K.
    BIOCONJUGATE CHEMISTRY, 2009, 20 (07) : 1383 - 1389
  • [47] Site-specific incorporation of quadricyclane into a protein and photocleavage of the quadricyclane ligation adduct
    Tomlin, Frederick M.
    Gordon, Chelsea G.
    Han, Yisu
    Wu, Taia S.
    Sletten, Ellen M.
    Bertozzi, Carolyn R.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2018, 26 (19) : 5280 - 5290
  • [48] Tracking down protein-protein interactions via a FRET-system using site-specific thiol-Labeling
    Soveges, B.
    Imre, T.
    Poti, A. L.
    Sok, P.
    Kele, Zs
    Alexa, A.
    Kele, P.
    Nemeth, K.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (32) : 5756 - 5763
  • [49] Near-native, site-specific and purification-free protein labeling for quantitative protein interaction analysis by MicroScale Thermophoresis
    Bartoschik, Tanja
    Galinec, Stefanie
    Kleusch, Christian
    Walkiewicz, Katarzyna
    Breitsprecher, Dennis
    Weigert, Sebastian
    Muller, Yves A.
    You, Changjiang
    Piehler, Jacob
    Vercruysse, Thomas
    Daelemans, Dirk
    Tschammer, Nuska
    SCIENTIFIC REPORTS, 2018, 8
  • [50] Generation of an intramolecular three-color fluorescence resonance energy transfer probe by site-specific protein labeling
    Voss, Stephanie
    Zhao, Lei
    Chen, Xi
    Gerhard, Frank
    Wu, Yao-Wen
    JOURNAL OF PEPTIDE SCIENCE, 2014, 20 (02) : 115 - 120
12345