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Deprotection Bases as an Alternative to the Traditional Bases Used in Solid-Phase Peptide Synthesis

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Autor(es):
de Arruda Brasil, Maria Carolina Oliveira ; Princival, Cleverson Rogerio ; Kuchenbecker, Vinicius ; Katekawa, Edson ; Magalhaes, Wagner Vidal ; Cilli, Eduardo Maffud
Número total de Autores: 6
Tipo de documento: Artigo Científico
Fonte: PROTEIN AND PEPTIDE LETTERS; v. N/A, p. 6-pg., 2025-11-04.
Resumo

Background The use of peptides in the pharmaceutical and cosmetic industries is attracting increasing attention. Most of the peptides currently marketed are obtained by chemical processes, most frequently solid-phase peptide synthesis (SPPS).Objective Although SPPS is efficient, it requires hazardous solvents, such as N,N-dimethylformamide, dichloromethane, and N-methylpyrrolidone, as well as the bases piperidine and 4-methylpiperidine in the deprotection step. This study presents two alternative reagents, 2-aminoethanol and 2-amino-2-methyl-1-propanol, for the removal of the fluorenyl-methyloxycarbonyl protecting group used in SPPS.Methods The traditional and alternative green SPPS using Fmoc protocol were employed.Results The synthesis of two peptides showed that the 2-aminoethanol and 2-amino-2-methyl-1-propanol are viable replacements for piperidine-derived reagents in peptide synthesis.Discussion The use of these reagents in SPPS afforded two peptides in high yield in an environmentally sustainable solvent.Conclusion The reagents are thus promising alternatives to piperidine derivatives, particularly 2-amino-2-methyl-1-propanol, in SPPS. (AU)

Processo FAPESP: 22/05411-8 - Desenvolvimento de bioconjugados peptídeos/guanidinas com atividade anti-Leishmania
Beneficiário:Eduardo Maffud Cilli
Modalidade de apoio: Auxílio à Pesquisa - Regular