title: New chemistries for chemoselective peptide ligations and the total synthesis of proteins.
abstract: The identification of fast, chemoselective bond-forming reactions is one of the major contemporary challenges in chemistry. The requirements of the native chemical ligation - an N-terminal cysteine and C-terminal thioesters - have encouraged a search for alternative amide-forming ligation reactions. Among successful alternatives to native chemical ligation, are the α-ketoacid-hydroxylamine ligation with 5-oxaproline and, serine/threonine ligation, and potassium acyltrifluoroborate (KAT) ligation. In addition, the KAT ligation, along with the non-amide forming alkyne-azide ligation, is very useful for synthetic conjugations. All of these recent ligation methods were applied to synthesize different proteins, and have allowed chemists to incorporate unnatural amino acids, or to modify the peptide backbone.
authors.affiliation: Laboratory für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH Zürich, Zürich 8093, Switzerland.
authors.forename: Thibault J R
authors.initials: TJ
authors.lastname: Harmand
authors.affiliation: Laboratory für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH Zürich, Zürich 8093, Switzerland.
authors.forename: Claudia E
authors.initials: CE
authors.lastname: Murar
authors.affiliation: Laboratory für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH Zürich, Zürich 8093, Switzerland; Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya 464-8602, Japan. Electronic address: bode@org.chem.ethz.ch.
authors.forename: Jeffrey W
authors.initials: JW
authors.lastname: Bode
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry; D000595:Amino Acid Sequence; D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D011506:Proteins / Q000138:chemical synthesis* / Q000737:chemistry; D012694:Serine / Q000138:chemical synthesis / Q000737:chemistry; D013912:Threonine / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000480:Alkynes; D001386:Azides; D010455:Peptides; D011506:Proteins; D013912:Threonine; C057984:5-oxaproline; D012694:Serine; D011392:Proline