title: Highly stereoselective recognition and deracemization of amino acids by supramolecular self-assembly.
abstract: The highly stereoselective supramolecular self-assembly of α-amino acids with a chiral aldehyde derived from binol and a chiral guanidine derived from diphenylethylenediamine (dpen) to form the imino acid salt is reported. This system can be used to cleanly convert D-amino acids into L-amino acids or vice versa at ambient temperature. It can also be used to synthesize α-deuterated D- or L-amino acids. A crystal structure of the ternary complex together with DFT computation provided detailed insight into the origin of the stereoselective recognition of amino acids.
authors.affiliation: Department of Chemistry, University of Toronto, 80 St George Street, Toronto, ON, M5S 3H6 (Canada) http://www.diaminopharm.com.
authors.forename: Soon Mog
authors.initials: SM
authors.lastname: So
authors.forename: Kimia
authors.initials: K
authors.lastname: Moozeh
authors.forename: Alan J
authors.initials: AJ
authors.lastname: Lough
authors.forename: Jik
authors.initials: J
authors.lastname: Chin
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003903:Deuterium / Q000737:chemistry; D019791:Guanidine / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D003903:Deuterium; D019791:Guanidine
keywords: amino acids; molecular recognition; stereoinversion; stereoselectivity; supramolecular self-assembly