Automatic procedures for the synthesis of difficult peptides using oxyma as activating reagent: A comparative study on the use of bases and on different deprotection and agitation conditions

Peptides
A CaporaleM Ruvo

Abstract

Solid-Phase Peptide Synthesis (SPPS) is a rapid and efficient methodology for the chemical synthesis of peptides and small proteins. However, the assembly of peptide sequences classified as "difficult" poses severe synthetic problems in SPPS for the occurrence of extensive aggregation of growing peptide chains which often leads to synthesis failure. In this framework, we have investigated the impact of different synthetic procedures on the yield and final purity of three well-known "difficult peptides" prepared using oxyma as additive for the coupling steps. In particular, we have comparatively investigated the use of piperidine and morpholine/DBU as deprotection reagents, the addition of DIPEA, collidine and N-methylmorpholine as bases to the coupling reagent. Moreover, the effect of different agitation modalities during the acylation reactions has been investigated. Data obtained represent a step forward in optimizing strategies for the synthesis of "difficult peptides".

Citations

Jan 27, 2019·Chemistry, an Asian Journal·Kyriakos G Varnava, Vijayalekshmi Sarojini
Mar 28, 2020·The Biochemical Journal·Emanuela IaccarinoAnnamaria Sandomenico
Jan 16, 2020·International Journal of Molecular Sciences·Valeria TaralloSandro De Falco
Jan 27, 2019·Journal of Peptide Science : an Official Publication of the European Peptide Society·Andrea CaporaleMenotti Ruvo
Dec 2, 2020·International Journal of Molecular Sciences·Mariangela VallettaAngela Chambery
May 3, 2021·Protein Science : a Publication of the Protein Society·José M PereiraSérgio M Santos

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