title: Boc-SPPS: Compatible Linker for the Synthesis of Peptide o-Aminoanilides.
abstract: A protection strategy is described for the efficient synthesis of peptide o-aminoanilides using in situ neutralization protocols for Boc-SPPS. On-resin protection of Boc-protected aminoacyl o-aminoanilides is achieved with 2-chlorobenzyl chloroformate. Activation through a peptidyl-benzotriazole intermediate allows for facile conversion to peptide-thioesters for use in native chemical ligation. In addition to providing a robust alternative to established thioester resins, as a latent thioester, the peptide o-aminoanilide has broad utility in convergent ligation strategies.
authors.affiliation: Division of Functional Genome Analysis, Deutsches Krebsforschungszentrum , Im Neuenheimer Feld 580, 69120 Heidelberg, Germany.|Departments of Chemistry and Cell & Molecular Biology, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Joachim
authors.initials: J
authors.lastname: Weidmann
authors.affiliation: Departments of Chemistry and Cell & Molecular Biology, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Elena
authors.initials: E
authors.lastname: Dimitrijević
authors.affiliation: Division of Functional Genome Analysis, Deutsches Krebsforschungszentrum , Im Neuenheimer Feld 580, 69120 Heidelberg, Germany.
authors.forename: Jörg D
authors.initials: JD
authors.lastname: Hoheisel
authors.affiliation: Departments of Chemistry and Cell & Molecular Biology, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Philip E
authors.initials: PE
authors.lastname: Dawson
mesh_terms: D000813:Anilides / Q000138:chemical synthesis* / Q000737:chemistry; D001710:Biotin / Q000737:chemistry; D004952:Esters; D064451:Hepcidins / Q000737:chemistry; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000813:Anilides; D004952:Esters; D064451:Hepcidins; D010455:Peptides; D001710:Biotin