title: Phosphothreonine as a catalytic residue in peptide-mediated asymmetric transfer hydrogenations of 8-aminoquinolines.
abstract: Phosphothreonine (pThr) was found to constitute a new class of chiral phosphoric acid (CPA) catalyst upon insertion into peptides. To demonstrate the potential of these phosphopeptides as asymmetric catalysts, enantioselective transfer hydrogenations of a previously underexplored substrate class for CPA-catalyzed reductions were carried out. pThr-containing peptides lead to the observation of enantioselectivities of up to 94:6 e.r. with 2-substituted quinolines containing C8-amino functionality. NMR studies indicate that hydrogen-bonding interactions promote strong complexation between substrates and a rigid β-turn catalyst.
authors.affiliation: Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06511 (USA).
authors.forename: Christopher R
authors.initials: CR
authors.lastname: Shugrue
authors.affiliation: Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06511 (USA). scott.miller@yale.edu.
authors.forename: Scott J
authors.initials: SJ
authors.lastname: Miller
mesh_terms: D000634:Aminoquinolines / Q000737:chemistry*; D020134:Catalytic Domain; D006859:Hydrogen / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D010769:Phosphothreonine / Q000737:chemistry*
chemical_list: D000634:Aminoquinolines; D010455:Peptides; D010769:Phosphothreonine; D006859:Hydrogen; C080436:8-aminoquinoline
keywords: asymmetric catalysis; peptides; phosphothreonine; quinoline; transfer hydrogenation