299208-69-8Relevant academic research and scientific papers
Enantioselective synthesis of the carbacephem antibiotic loracarbef via Mitsunobu and Dieckmann cyclization from an unnatural amino acid
Misner, Jerry W.,Fisher, Jack W.,Gardner, John P.,Pedersen, Steve W.,Trinkle, Kristina L.,Jackson, Billy G.,Zhang, Tony Y.
, p. 5991 - 5993 (2007/10/03)
The nucleus of the carbacephem antibiotic loracarbef was synthesized in a highly efficient and enantioselective fashion from 2S,3S-2-amino-3-hydroxy-6-heptenoic acid (AHHA), which was derived from enzyme-catalyzed condensation of glycine and 4-pentenaldehyde. The bicyclic framework of this compound was established through sequential Mitsunobu reaction and aldol condensations.
Enantioselective syntheses of 1-carbacephalosporins from chemoenzymically derived β-hydroxy-α-amino acids: Applications to the total synthesis of carbacephem antibiotic loracarbef
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.
, p. 5667 - 5677 (2007/10/03)
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. (C) 2000 Elsevier Science Ltd.
