Enantioselective syntheses of 1-carbacephalosporins from chemoenzymically derived beta-hydroxy-alpha-amino acids: Applications to the total synthesisof carbacephem antibiotic loracarbef

Authors
Jackson, BG Pedersen, SW Fisher, JW Misner, JW Gardner, JP Staszak, MA Doecke, C Rizzo, J Aikins, J Farkas, E Trinkle, KL Vicenzi, J Reinhard, M Kroeff, EP Higginbotham, CA Gazak, RJ Zhang, TY
Citation
Bg. Jackson et al., Enantioselective syntheses of 1-carbacephalosporins from chemoenzymically derived beta-hydroxy-alpha-amino acids: Applications to the total synthesisof carbacephem antibiotic loracarbef, TETRAHEDRON, 56(31), 2000, pp. 5667-5677
Citations number
57
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
31
Year of publication
2000
Pages
5667 - 5677
Database
ISI
SICI code
0040-4020(20000728)56:31<5667:ESO1FC>2.0.ZU;2-2
Abstract
Serine hydroxymethyltransferase (SHMT) derived from recombinant E. coli was found to be able to catalyze the condensation between glycine and 4-penten aldehyde, affording enantiopure L-erythro-2-amino-3-hydroxy-6-heptenoic aci d (AHHA) in high yield and throughput. Conversion of this chiral intermedia te of biosynthetic origin to the oral carbacephalosporin antibiotic loracar bef (Lorabid(R)) via beta-lactam forming reactions and subsequent Dieckmann cyclization was achieved. (C) 2000 Elsevier Science Ltd. All rights reserv ed.