Tetrahedron

Enantioselective syntheses of 1-carbacephalosporins from chemoenzymically derived β-hydroxy-α-amino acids: applications to the total synthesis of carbacephem …

…, J Aikins, E Farkas, KL Trinkle, J Vicenzi, M Reinhard…

Index: Jackson, Billy G.; Pedersen, Steve W.; Fisher, Jack W.; Misner, Jerry W.; Gardner, John P.; Staszak, Michael A.; Doecke, Christopher; Rizzo, John; Aikins, James; Farkas, Eugene; Trinkle, Kristina L.; Vicenzi, Jeffrey; Reinhard, Matt; Kroeff, Eugene P.; Higginbotham, Chris A.; Gazak; Zhang, Tony Y. Tetrahedron, 2000 , vol. 56, # 31 p. 5667 - 5677

Full Text: HTML

Citation Number: 27

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 ...