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Chapter 80,065

Side-Chain Anchoring Strategies for the Synthesis of Peptide Thioesters and Selenoesters

Kambanis, L.; Kulkarni, S.S.; Payne, R.J.

Methods in Molecular Biology 2530: 125-140

2022


ISSN/ISBN: 1940-6029
PMID: 35761046
Accession: 080064529

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Peptides bearing C-terminal thioester and selenoester functionalities are essential precursors for the chemical synthesis of larger proteins using ligation chemistry, including native chemical ligation (NCL) and diselenide-selenoester ligation (DSL). The use of a side-chain anchoring thioesterification or selenoesterification approach offers a robust method to access peptide thioesters or peptide selenoesters in excellent yields and in high purity. Importantly, this methodology overcomes solubility issues and epimerization of the C-terminal amino acid residue that can occur using solution-phase approaches. Detailed methods for the solid-phase synthesis of peptide thioesters and selenoesters using a side-chain anchoring approach are outlined in this article.

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