Chemoselective peptide backbone diversification and bioorthogonal ligation by ruthenium-catalyzed C-H activation/annulation
- Author
- Liangliang Song, Gerardo M. Ojeda-Carralero, Divyaakshar Parmar, David A. Gonzalez-Martinez, Luc Van Meervelt, Johan Van der Eycken (UGent) , Jan Goeman (UGent) , Daniel G. Rivera and Erik V. Van der Eycken
- Organization
- Abstract
- The field of peptide derivatization by metal-catalyzed C-H activation has been mostly directed to modify the side chains, but poor attention has been given to the peptide backbone. Here we report a ruthenium-catalyzed C-H activation/annulation process that can chemoselectively modify the peptide backbone producing functionalized isoquinolone scaffolds with high regioselectivity in a rapid and step-economical manner. This strategy is characterized by racemization-free conditions and the production of fluorescent peptides, and peptide conjugates to drugs, natural products and other peptide fragments, providing a chemical approach for the construction of novel peptide-pharmacophore conjugates. Mechanistic studies suggest that amide bonds of peptide backbone act as the bidentate directing group to promote the C-H activation/annulation process. This report provides an unprecedented example of peptide backbone diversification and bioorthogonal ligation exploiting the power of ruthenium-catalyzed C-H activation.
- Keywords
- Peptides, C-H Activation, Metal catalysis, Ruthenium, Annulation, AMINO-ACIDS, FUNCTIONALIZATION, ACTIVATION, MACROCYCLIZATION, CYCLIZATION, ALKYLATION, ANNULATION, STRATEGIES, LIGAND
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-8721577
- MLA
- Song, Liangliang, et al. “Chemoselective Peptide Backbone Diversification and Bioorthogonal Ligation by Ruthenium-Catalyzed C-H Activation/Annulation.” ADVANCED SYNTHESIS & CATALYSIS, vol. 363, no. 13, 2021, pp. 3297–304, doi:10.1002/adsc.202100323.
- APA
- Song, L., Ojeda-Carralero, G. M., Parmar, D., Gonzalez-Martinez, D. A., Van Meervelt, L., Van der Eycken, J., … Van der Eycken, E. V. (2021). Chemoselective peptide backbone diversification and bioorthogonal ligation by ruthenium-catalyzed C-H activation/annulation. ADVANCED SYNTHESIS & CATALYSIS, 363(13), 3297–3304. https://doi.org/10.1002/adsc.202100323
- Chicago author-date
- Song, Liangliang, Gerardo M. Ojeda-Carralero, Divyaakshar Parmar, David A. Gonzalez-Martinez, Luc Van Meervelt, Johan Van der Eycken, Jan Goeman, Daniel G. Rivera, and Erik V. Van der Eycken. 2021. “Chemoselective Peptide Backbone Diversification and Bioorthogonal Ligation by Ruthenium-Catalyzed C-H Activation/Annulation.” ADVANCED SYNTHESIS & CATALYSIS 363 (13): 3297–3304. https://doi.org/10.1002/adsc.202100323.
- Chicago author-date (all authors)
- Song, Liangliang, Gerardo M. Ojeda-Carralero, Divyaakshar Parmar, David A. Gonzalez-Martinez, Luc Van Meervelt, Johan Van der Eycken, Jan Goeman, Daniel G. Rivera, and Erik V. Van der Eycken. 2021. “Chemoselective Peptide Backbone Diversification and Bioorthogonal Ligation by Ruthenium-Catalyzed C-H Activation/Annulation.” ADVANCED SYNTHESIS & CATALYSIS 363 (13): 3297–3304. doi:10.1002/adsc.202100323.
- Vancouver
- 1.Song L, Ojeda-Carralero GM, Parmar D, Gonzalez-Martinez DA, Van Meervelt L, Van der Eycken J, et al. Chemoselective peptide backbone diversification and bioorthogonal ligation by ruthenium-catalyzed C-H activation/annulation. ADVANCED SYNTHESIS & CATALYSIS. 2021;363(13):3297–304.
- IEEE
- [1]L. Song et al., “Chemoselective peptide backbone diversification and bioorthogonal ligation by ruthenium-catalyzed C-H activation/annulation,” ADVANCED SYNTHESIS & CATALYSIS, vol. 363, no. 13, pp. 3297–3304, 2021.
@article{8721577,
abstract = {{The field of peptide derivatization by metal-catalyzed C-H activation has been mostly directed to modify the side chains, but poor attention has been given to the peptide backbone. Here we report a ruthenium-catalyzed C-H activation/annulation process that can chemoselectively modify the peptide backbone producing functionalized isoquinolone scaffolds with high regioselectivity in a rapid and step-economical manner. This strategy is characterized by racemization-free conditions and the production of fluorescent peptides, and peptide conjugates to drugs, natural products and other peptide fragments, providing a chemical approach for the construction of novel peptide-pharmacophore conjugates. Mechanistic studies suggest that amide bonds of peptide backbone act as the bidentate directing group to promote the C-H activation/annulation process. This report provides an unprecedented example of peptide backbone diversification and bioorthogonal ligation exploiting the power of ruthenium-catalyzed C-H activation.}},
author = {{Song, Liangliang and Ojeda-Carralero, Gerardo M. and Parmar, Divyaakshar and Gonzalez-Martinez, David A. and Van Meervelt, Luc and Van der Eycken, Johan and Goeman, Jan and Rivera, Daniel G. and Van der Eycken, Erik V.}},
issn = {{1615-4150}},
journal = {{ADVANCED SYNTHESIS & CATALYSIS}},
keywords = {{Peptides,C-H Activation,Metal catalysis,Ruthenium,Annulation,AMINO-ACIDS,FUNCTIONALIZATION,ACTIVATION,MACROCYCLIZATION,CYCLIZATION,ALKYLATION,ANNULATION,STRATEGIES,LIGAND}},
language = {{eng}},
number = {{13}},
pages = {{3297--3304}},
title = {{Chemoselective peptide backbone diversification and bioorthogonal ligation by ruthenium-catalyzed C-H activation/annulation}},
url = {{http://doi.org/10.1002/adsc.202100323}},
volume = {{363}},
year = {{2021}},
}
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