ArticleChemistry (Weinheim an der Bergstrasse, Germany)2017
Exploiting the MeDbz Linker To Generate Protected or Unprotected C-Terminally Modified Peptides.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Review on the o-Aminoaniline Moiety in Peptide and Protein Chemistry.Chembiochem : a European journal of chemical biology · 2025Review
- Synthesis of Anabaenopeptins With a Strategic Eye Toward N-Terminal Sequence Diversity.Journal of peptide science : an official publication of the European Peptide Society · 2025Article
- Safety-Catch Linkers for Solid-Phase Peptide Synthesis.Molecules (Basel, Switzerland) · 2024Review
- Selective Conversion of Unactivated C-N Amide Bond to C-C bond via Steric and Electronic Resonance Destabilization.Organic letters · 2022Article
- Recent advances in the synthesis of C-terminally modified peptides.Organic & biomolecular chemistry · 2020Review
- Solid-Phase Synthesis of Head to Side-Chain Tyr-Cyclodepsipeptides Through a Cyclative Cleavage From Fmoc-MeDbz/MeNbz-resins.Frontiers in chemistry · 2020Article
- Sequence Diversification by Divergent C-Terminal Elongation of Peptides.The Journal of organic chemistry · 2018Article
- Epimerization-free access to C-terminal cysteine peptide acids, carboxamides, secondary amides, and estersChemical science · 2018Article
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Authors and funding
4 authors.
Funding
Abstract
C-terminally modified peptides are important targets for pharmaceutical and biochemical applications. Known methods for C-terminal diversification are limited mainly in terms of the scope of accessible modifications or by epimerization of the C-terminal amino acid. In this work, we present a broadly applicable approach that enables access to a variety of C-terminally functionalized peptides in either protected or unprotected form. This chemistry proceeds without epimerization of C-terminal Ala and tolerates nucleophiles of varying nucleophilicity. Finally, unprotected peptides bearing nucleophilic side chain groups can be selectively functionalized by strong nucleophiles, whereas macrocyclization is observed for weaker nucleophiles. The potential utility of this method is demonstrated through the divergent synthesis of the conotoxin conopressin G and GLP-1(7-36) and analogs.
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