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Issue 37, 2020

Recent advances in the synthesis of C-terminally modified peptides

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Abstract

C-Terminally modified peptides are important for the development and delivery of peptide-based pharmaceuticals because they impact peptide activity, stability, hydrophobicity, and membrane permeability. Additionally, the vulnerability of C-terminal esters to cleavage by endogenous esterases makes them excellent pro-drugs. Methods for post-SPPS C-terminal functionalization potentially enable access to libraries of modified peptides, facilitating tailoring of their solubility, potency, toxicity, and uptake pathway. Apparently minor structural changes can significantly impact the binding, folding, and pharmacokinetics of the peptide. This review summarizes developments in chemical methods for C-terminal modification of peptides published since the last review on this topic in 2003.

Graphical abstract: Recent advances in the synthesis of C-terminally modified peptides

Article information


Submitted
09 Jul 2020
Accepted
02 Sep 2020
First published
02 Sep 2020

Org. Biomol. Chem., 2020,18, 7253-7272
Article type
Review Article

Recent advances in the synthesis of C-terminally modified peptides

C. A. Arbour, L. G. Mendoza and J. L. Stockdill, Org. Biomol. Chem., 2020, 18, 7253 DOI: 10.1039/D0OB01417F

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