Solid Phase Peptide Synthesis (SPPS) is a key technology for the production of pharmaceutical grade peptides, although it represents the worst modality in the pharma segment when considering its Process Mass Intensity (PMI). Consequently, academic and industrial research teams have focused their attention on greening SPPS protocols by introducing more sustainable alternatives to the most common reagents and solvents. In this context, 3-(diethylamino)propylamine (DEAPA) was identified to be a viable alternative to piperidine for Fmoc removal. In addition, the use of DEAPA in N-octyl-pyrrolidone (manual synthesis) or N-octyl pyrrolidone/dimethyl carbonate 8/2 v/v (automated synthesis) was proved to be able to minimize the formation of side products like diastereoisomers and aspartimide-containing derivatives.

Replacing piperidine in Solid Phase Peptide Synthesis: effective Fmoc removal by alternative bases / Giulia Martelli; Paolo Cantelmi; Chiara Palladino; Alexia Mattellone; Dario Corbisiero; Tommaso Fantoni; Alessandra Tolomelli; Marco Macis; Antonio Ricci; Walter Cabri; Lucia Ferrazzano. - In: GREEN CHEMISTRY. - ISSN 1463-9270. - ELETTRONICO. - 23:20(2021), pp. 8096-8107. [10.1039/d1gc02634h]

Replacing piperidine in Solid Phase Peptide Synthesis: effective Fmoc removal by alternative bases

Giulia Martelli;Chiara Palladino;Alexia Mattellone;Dario Corbisiero;Tommaso Fantoni;Alessandra Tolomelli
;
Walter Cabri
;
Lucia Ferrazzano
2021

Abstract

Solid Phase Peptide Synthesis (SPPS) is a key technology for the production of pharmaceutical grade peptides, although it represents the worst modality in the pharma segment when considering its Process Mass Intensity (PMI). Consequently, academic and industrial research teams have focused their attention on greening SPPS protocols by introducing more sustainable alternatives to the most common reagents and solvents. In this context, 3-(diethylamino)propylamine (DEAPA) was identified to be a viable alternative to piperidine for Fmoc removal. In addition, the use of DEAPA in N-octyl-pyrrolidone (manual synthesis) or N-octyl pyrrolidone/dimethyl carbonate 8/2 v/v (automated synthesis) was proved to be able to minimize the formation of side products like diastereoisomers and aspartimide-containing derivatives.
2021
Replacing piperidine in Solid Phase Peptide Synthesis: effective Fmoc removal by alternative bases / Giulia Martelli; Paolo Cantelmi; Chiara Palladino; Alexia Mattellone; Dario Corbisiero; Tommaso Fantoni; Alessandra Tolomelli; Marco Macis; Antonio Ricci; Walter Cabri; Lucia Ferrazzano. - In: GREEN CHEMISTRY. - ISSN 1463-9270. - ELETTRONICO. - 23:20(2021), pp. 8096-8107. [10.1039/d1gc02634h]
Giulia Martelli; Paolo Cantelmi; Chiara Palladino; Alexia Mattellone; Dario Corbisiero; Tommaso Fantoni; Alessandra Tolomelli; Marco Macis; Antonio Ricci; Walter Cabri; Lucia Ferrazzano
File in questo prodotto:
File Dimensione Formato  
Replacing post print.pdf

Open Access dal 07/09/2022

Tipo: Postprint
Licenza: Licenza per Accesso Aperto. Altra tipologia di licenza compatibile con Open Access
Dimensione 740.07 kB
Formato Adobe PDF
740.07 kB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/835787
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 17
  • ???jsp.display-item.citation.isi??? 15
social impact