title: Incorporation of Acid-Labile Masking Groups for the Traceless Synthesis of C-Terminal Peptide α-Ketoacids.
abstract: An optimized protocol for the masking of α-ketoacids with acid-labile cyclic acetal protecting groups is reported. Unlike prior approaches, these new conditions allow the synthesis of protected α-ketoacids bearing aromatic, hindered alkyl, and protected polar side chains. Attachment to a Wang-type linker and solid support provides a resin that delivers fully unprotected C-terminal peptide α-ketoacids upon resin cleavage. These peptides are the key starting materials for chemical protein synthesis using the α-ketoacid-hydroxylamine ligation.
authors.affiliation: Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich , 8093 Zürich, Switzerland.|Institute of Transformative bio-Molecules (WPI-ITbM), Nagoya University , Chikusa, Nagoya 464-8602, Japan.
authors.forename: Frédéric
authors.initials: F
authors.lastname: Thuaud
authors.affiliation: Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich , 8093 Zürich, Switzerland.
authors.forename: Florian
authors.initials: F
authors.lastname: Rohrbacher
authors.affiliation: Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich , 8093 Zürich, Switzerland.
authors.forename: André
authors.initials: A
authors.lastname: Zwicky
authors.affiliation: Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich , 8093 Zürich, Switzerland.|Institute of Transformative bio-Molecules (WPI-ITbM), Nagoya University , Chikusa, Nagoya 464-8602, Japan.
authors.forename: Jeffrey W
authors.initials: JW
authors.lastname: Bode
mesh_terms: D006898:Hydroxylamines / Q000737:chemistry*; D007651:Keto Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006898:Hydroxylamines; D007651:Keto Acids; D010455:Peptides; C000601200:alpha-ketoacid-hydroxylamine