title: Tidbits for the synthesis of bis(2-sulfanylethyl)amido (SEA) polystyrene resin, SEA peptides and peptide thioesters.
abstract: Protein total chemical synthesis enables the atom-by-atom control of the protein structure and therefore has a great potential for studying protein function. Native chemical ligation of C-terminal peptide thioesters with N-terminal cysteinyl peptides and related methodologies are central to the field of protein total synthesis. Consequently, methods enabling the facile synthesis of peptide thioesters using Fmoc-SPPS are of great value. Herein, we provide a detailed protocol for the preparation of bis(2-sulfanylethyl)amino polystyrene resin as a starting point for the synthesis of C-terminal bis(2-sulfanylethyl)amido peptides and of peptide thioesters derived from 3-mercaptopropionic acid.
authors.affiliation: UMR CNRS 8161, Pasteur Institute of Lille, Univ. Lille Nord de France, 1 rue du Pr Calmette, 59021, Lille, France.
authors.forename: Nathalie
authors.initials: N
authors.lastname: Ollivier
authors.affiliation: UMR CNRS 8161, Pasteur Institute of Lille, Univ. Lille Nord de France, 1 rue du Pr Calmette, 59021, Lille, France.
authors.forename: Laurent
authors.initials: L
authors.lastname: Raibaut
authors.affiliation: UMR CNRS 8161, Pasteur Institute of Lille, Univ. Lille Nord de France, 1 rue du Pr Calmette, 59021, Lille, France.
authors.forename: Annick
authors.initials: A
authors.lastname: Blanpain
authors.affiliation: UMR CNRS 8161, Pasteur Institute of Lille, Univ. Lille Nord de France, 1 rue du Pr Calmette, 59021, Lille, France.
authors.forename: Rémi
authors.initials: R
authors.lastname: Desmet
authors.affiliation: UMR CNRS 8161, Pasteur Institute of Lille, Univ. Lille Nord de France, 1 rue du Pr Calmette, 59021, Lille, France.
authors.forename: Julien
authors.initials: J
authors.lastname: Dheur
authors.affiliation: UMR CNRS 8161, Pasteur Institute of Lille, Univ. Lille Nord de France, 1 rue du Pr Calmette, 59021, Lille, France.
authors.forename: Reda
authors.initials: R
authors.lastname: Mhidia
authors.affiliation: UMR CNRS 8161, Pasteur Institute of Lille, Univ. Lille Nord de France, 1 rue du Pr Calmette, 59021, Lille, France.
authors.forename: Emmanuelle
authors.initials: E
authors.lastname: Boll
authors.affiliation: UMR CNRS 8161, Pasteur Institute of Lille, Univ. Lille Nord de France, 1 rue du Pr Calmette, 59021, Lille, France.
authors.forename: Hervé
authors.initials: H
authors.lastname: Drobecq
authors.affiliation: UMR CNRS 8161, Pasteur Institute of Lille, Univ. Lille Nord de France, 1 rue du Pr Calmette, 59021, Lille, France.
authors.forename: Silvain L
authors.initials: SL
authors.lastname: Pira
authors.affiliation: UMR CNRS 8161, Pasteur Institute of Lille, Univ. Lille Nord de France, 1 rue du Pr Calmette, 59021, Lille, France.
authors.forename: Oleg
authors.initials: O
authors.lastname: Melnyk
mesh_terms: D060326:Chemistry Techniques, Synthetic; D004952:Esters / Q000138:chemical synthesis*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011137:Polystyrenes / Q000138:chemical synthesis* / Q000737:chemistry; D012117:Resins, Synthetic / Q000138:chemical synthesis* / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry
chemical_list: D004952:Esters; D010455:Peptides; D011137:Polystyrenes; D012117:Resins, Synthetic; D013449:Sulfonamides
keywords: Fmoc‐SPPS; bis(2‐sulfanylethyl)amido (SEA); thioester; thiol exchange