A novel PEG-based solid support enables the synthesis of > 50 amino acids peptide thioesters and the total synthesis of a functional SUMO-1 peptide conjugate

Emmanuelle Boll (1) , Hervé Drobecq (2) , Nathalie Ollivier (2) , Laurent Raibaut (2) , Rémi Desmet (2) , Jérome Vicogne (2) , Oleg Melnyk (2)

1 CBC
2 IBLI - Institut de biologie de Lille - IBL

A bis(2-sulfanylethyl)amino PEG-based resin enabled the synthesis of large (~50 Aa) SEA or thioester peptides using Fmoc-SPPS. These peptide segments permitted the first total synthesis of a 97 amino acids long SUMO-1-SEA peptide thioester surrogate and of a functional and reversible SUMO-1 peptide conjugate.

Mots clés: bis(2-sulfanylethyl)amido; SEA ligation; protein total synthesis; Small ubiquitin-like modifier; SUMO; post-translational modification; Ulp1

Domaines: Chimie organique

Emmanuelle Boll, Hervé Drobecq, Nathalie Ollivier, Laurent Raibaut, Rémi Desmet, et al.. A novel PEG-based solid support enables the synthesis of > 50 amino acids peptide thioesters and the total synthesis of a functional SUMO-1 peptide conjugate. Chemical Science, 2014, 5, pp.2017-2022. ⟨10.1039/C3SC53509F⟩. ⟨hal-00952546v3⟩