title: Semipermanent C-terminal carboxylic acid protecting group: application to solubilizing peptides and fragment condensation.
abstract: The 2-methoxy-4-methylsulfinylbenzyl alcohol (Mmsb-OH) safety-catch linker has been described as a useful tool to overcome two obstacles in peptide synthesis: the solubility and fragment condensation of peptides. The incorporation of the linker into an insoluble peptide target, thereby allowing the conjugation of a poly-Lys as a "solubilizing tag", notably enhanced the solubility of the peptide. The selective conditions that remove that linker favored its incorporation as a semipermanent C-terminal protecting group, thereby allowing fragment condensation of peptides.
authors.affiliation: Institute for Research in Biomedicine (IRB Barcelona) Barcelona, Baldiri Reixac 10, 08028 Barcelona, Spain.
authors.forename: Marta
authors.initials: M
authors.lastname: Paradís-Bas
authors.forename: Judit
authors.initials: J
authors.lastname: Tulla-Puche
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
mesh_terms: D000595:Amino Acid Sequence; D001592:Benzyl Alcohols / Q000737:chemistry*; D002264:Carboxylic Acids; D008239:Lysine / Q000737:chemistry*; D015394:Molecular Structure; D010446:Peptide Fragments / Q000138:chemical synthesis* / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C000600330:2-methoxy-4-methylsulfinylbenzyl alcohol; D001592:Benzyl Alcohols; D002264:Carboxylic Acids; D010446:Peptide Fragments; D010455:Peptides; D008239:Lysine