Tetrahedron p. 5667 - 5677 (2000)
Update date:2022-08-04
Topics: Final steps Stereochemistry Control Purification and Isolation Protection and Functionalization Side Chain Functionalization
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.
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.
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