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 :
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