• Title of article

    Enantioselective Syntheses of 1-Carbacephalosporins from Chemoenzymically Derived β-Hydroxy-α-Amino Acids: Applications to the Total Synthesis of Carbacephem Antibiotic Loracarbef

  • Author/Authors

    Billy G Jackson، نويسنده , , Steve W Pedersen، نويسنده , , Jack W Fisher، نويسنده , , Jerry W. Misner، نويسنده , , John P Gardner، نويسنده , , Michael A Staszak، نويسنده , , Christopher Doecke، نويسنده , , John Rizzo، نويسنده , , James Aikins، نويسنده , , Eugene Farkas، نويسنده , , Kristina L Trinkle، نويسنده , , Jeffrey Vicenzi، نويسنده , , Matt Reinhard، نويسنده , , Eugene P Kroeff، نويسنده , , Chris A Higginbotham، نويسنده , , R.، نويسنده ,

  • Issue Information
    هفته نامه با شماره پیاپی سال 2000
  • Pages
    11
  • From page
    5667
  • To page
    5677
  • Abstract
    Serine hydroxymethyltransferase (SHMT) derived from recombinant E. coli was found to be able to catalyze the condensation between glycine and 4-pentenaldehyde, affording enantiopure l-erythro-2-amino-3-hydroxy-6-heptenoic acid (AHHA) in high yield and throughput. Conversion of this chiral intermediate of biosynthetic origin to the oral carbacephalosporin antibiotic loracarbef (Lorabid®) via β-lactam forming reactions and subsequent Dieckmann cyclization was achieved.
  • Keywords
    SHMT , Aldolase , Biocatalysis , Cephalosporins , carbacephalosporins , ?-hydroxy-?-amino acid , ?-lactam , loracarbef , serine hydroxymethyltransferase , Antibacterials
  • Journal title
    Tetrahedron
  • Serial Year
    2000
  • Journal title
    Tetrahedron
  • Record number

    1081062

    • Link To Document
    https://search.isc.ac/dl/search/defaultta.aspx?DTC=10&DC=1081062