title: Synthesis of L-4,4-difluoroglutamic acid via nucleophilic addition to a chiral aldehyde.
abstract: Fluorine-containing derivatives of amino acids are assuming increasing importance as probes of biological function and enzyme mechanism. We now report a new, flexible route to enantiomerically pure L-4,4-difluoroglutamic acid that exploits the addition of difluorinated nucleophiles to configurationally stable alpha-aminoaldehydes. Conversion of the difluorinated adducts to L-4,4-difluoroglutamic acid can be accomplished in three steps by Barton-McCombie dehydroxylation and acid hydrolysis.
authors.affiliation: Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA.
authors.forename: Y
authors.initials: Y
authors.lastname: Ding
authors.forename: J
authors.initials: J
authors.lastname: Wang
authors.forename: K A
authors.initials: KA
authors.lastname: Abboud
authors.forename: Y
authors.initials: Y
authors.lastname: Xu
authors.forename: W R
authors.initials: WR
authors.lastname: Dolbier
authors.forename: N G
authors.initials: NG
authors.lastname: Richards
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001217:Aspartate-Ammonia Ligase / Q000737:chemistry / Q000378:metabolism; D005971:Glutamates / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D006868:Hydrolysis; D006900:Hydroxylation; D008968:Molecular Conformation
chemical_list: D000447:Aldehydes; D005971:Glutamates; C097769:4,4-difluoroglutamic acid; D001217:Aspartate-Ammonia Ligase