title: Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a Mn(I)(bpy)(CO)3-coordinated azide.
abstract: The catalyst-free room temperature iClick reaction of an unsymmetrically 2,3-disubstituted oxanorbornadiene (OND) as a "masked" alkyne equivalent with [Mn(N3)(bpy(CH3,CH3))(CO)3] leads to isolation of a phenylalanine ester bioconjugate, in which the model amino acid is linked to the metal moiety via a N-2-coordinated triazolate formed in a cycloaddition-retro-Diels-Alder (crDA) reaction sequence, in a novel approach to bioorthogonal coupling reactions based on metal-centered reactivity.
authors.affiliation: Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany. peter.v.simpson@gmail.com ulrich.schatzschneider@uni-wuerzburg.de.
authors.forename: Lucas
authors.initials: L
authors.lastname: Henry
authors.forename: Christoph
authors.initials: C
authors.lastname: Schneider
authors.forename: Benedict
authors.initials: B
authors.lastname: Mützel
authors.forename: Peter V
authors.initials: PV
authors.lastname: Simpson
authors.forename: Christoph
authors.initials: C
authors.lastname: Nagel
authors.forename: Katharina
authors.initials: K
authors.lastname: Fucke
authors.forename: Ulrich
authors.initials: U
authors.lastname: Schatzschneider
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D001892:Camphanes / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry; D056831:Coordination Complexes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D008345:Manganese / Q000737:chemistry; D008968:Molecular Conformation; D010649:Phenylalanine / Q000737:chemistry; D013696:Temperature; D013816:Thermodynamics
chemical_list: D000480:Alkynes; D000596:Amino Acids; D001386:Azides; D001892:Camphanes; D056831:Coordination Complexes; D008345:Manganese; D010649:Phenylalanine