Synthesis of L-4,4-difluoroglutamic acid via nucleophilic addition to a chiral aldehyde.
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.
Ding
Y
Y
Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA.
Wang
J
J
Abboud
K A
KA
Xu
Y
Y
Dolbier
W R
WR
Richards
N G
NG
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
D000447:Aldehydes; D005971:Glutamates; C097769:4,4-difluoroglutamic acid; D001217:Aspartate-Ammonia Ligase