title: Cysteine pseudoprolines for thiol protection and peptide macrocyclization enhancement in Fmoc-based solid-phase peptide synthesis.
abstract: Contrary to other studies, here we describe cysteine (Cys) pseudoproline-containing peptides with short deprotection times in TFA. The deprotection times fell in the same range as other protecting groups commonly used in SPPS (e.g., 1-3 h). Moreover, when using Cys pseudoprolines as peptide macrocyclization-enhancing moieties a considerable reduction in reaction time was observed compared to a peptide containing trityl protected Cys.
authors.affiliation: Institute for Research in Biomedicine , 08028, Barcelona, Spain.
authors.forename: Tobias M
authors.initials: TM
authors.lastname: Postma
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
mesh_terms: D003500:Cyclization; D003545:Cysteine / Q000031:analogs & derivatives* / Q000737:chemistry*; D004151:Dipeptides / Q000737:chemistry*; D015394:Molecular Structure; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013844:Thiazoles / Q000737:chemistry*
chemical_list: D004151:Dipeptides; D013438:Sulfhydryl Compounds; D013844:Thiazoles; C505976:pseudoproline; D011392:Proline; D003545:Cysteine