Solid phase peptide synthesis using side-chain unprotected arginine and histidine with Oxyma Pure/TBEC in green solvents

The elimination of side-chain orthogonal protective groups of arginine and histidine is critical to improve solid phase peptide synthesis (SPPS) sustainability through an increase in the peptide atom economy (AE) and decrease in impurities generated during the final cleavage step. The combination of...

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Published inGreen chemistry : an international journal and green chemistry resource : GC
Main Authors Fantoni, Tommaso, Orlandin, Andrea, Di Stefano, Ilaria, Macis, Marco, Tolomelli, Alessandra, Ricci, Antonio, Cabri, Walter, Ferrazzano, Lucia
Format Journal Article
LanguageEnglish
Published 18.09.2024
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Summary:The elimination of side-chain orthogonal protective groups of arginine and histidine is critical to improve solid phase peptide synthesis (SPPS) sustainability through an increase in the peptide atom economy (AE) and decrease in impurities generated during the final cleavage step. The combination of Oxyma Pure and tertbutyl ethyl carbodiimide (TBEC) in the correct ratio allowed the use of side-chain free arginine and histidine in green solvents. Etelcalcetide and vasopressin intermediates as well as critical key fragments of liraglutide and semaglutide were successfully synthetized via SPPS using optimized conditions. In addition, the Oxyma Pure/TBEC protocol in NBP/DMC was successfully applied to a sequence containing side-chain unprotected arginine, histidine, tryptophan and tyrosine.
ISSN:1463-9262
1463-9270
DOI:10.1039/D4GC03209H