title: A rapid and efficient method for the synthesis of selectively S-Trt or S-Mmt protected Cys-containing peptides.
abstract: Selective removal of protecting groups under different cleavage mechanisms could be an asset in peptide synthesis, since it provides the feasibility to incorporate different functional groups in similar reactive centres. However, selective protection/deprotection of orthogonal protecting groups in peptides is still challenging, especially for Cys-containing peptides, where protection of the cysteine side-chain is mandatory since the nucleophilic thiol can be otherwise alkylated, acylated or oxidized. Herein, we established a protocol for the synthesis of Cys-selective S-Trt or S-Mmt protected Cys-containing peptides, in a rapid way. This was achieved by, simply fine-tuning the carbocation scavenger in the final acidolytic release of the peptide from the solid support in the classic SPPS.
authors.affiliation: Section of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, 45110, Ioanina, Greece.
authors.forename: Panagiotis
authors.initials: P
authors.lastname: Stathopoulos
authors.forename: Serafim
authors.initials: S
authors.lastname: Papas
authors.forename: Marianna
authors.initials: M
authors.lastname: Sakka
authors.forename: Andreas G
authors.initials: AG
authors.lastname: Tzakos
authors.forename: Vassilios
authors.initials: V
authors.lastname: Tsikaris
mesh_terms: D000215:Acylation; D000478:Alkylation; D003545:Cysteine / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D020011:Protective Agents / Q000737:chemistry*; D060327:Solid-Phase Synthesis Techniques / Q000379:methods*; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D009942:Organometallic Compounds; D010455:Peptides; D020011:Protective Agents; D013438:Sulfhydryl Compounds; C009907:2-methylcyclopentadienyl manganese tricarbonyl; D003545:Cysteine