63069-06-7Relevant academic research and scientific papers
Enzymatic synthesis of ω-carboxy-β-hydroxy-(l)-α-amino acids
Sagui, Francesca,Conti, Paola,Roda, Gabriella,Contestabile, Roberto,Riva, Sergio
, p. 5079 - 5084 (2008/09/21)
Commercially available ω-carboxy-aldehydes and glycine have been subjected to the catalytic action of an l-threonine aldolase from Escherichia coli to give the corresponding β-hydroxy-α-(l)-amino acids as a mixture of erythro/threo epimers. Specifically, the reaction with glyoxylic acid (2) gave the epimeric β-hydroxy-(l)-aspartates (t,e)-9 that could be isolated by ion-exchange chromatography in 67% yield. Following esterification and N-Boc protection, the two epimers could be isolated as pure compounds. Similarly, the aldolase-catalyzed addition of glycine to succinic semialdehyde (4) gave the expected mixture of β-hydroxy-l-α-aminoadipic acids (t)-12 and (e)-12 in 34% yield.
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.
