Industrial Biotransformations

Penicillin amidase
Escherichia coli
4) Process parameters
yield: 45 %
ee: > 99.9 %
reactor type: batch
down stream processing: filtration
company: Eli Lilly, USA
5) Product application
● The (2R,3S)-azetidinone is a key intermediate in the synthesis of loracarbef, a carbacephalosporin
antibiotic:
Fig. 3.5.1.11 – 2
● Loracarbef is a stable analog of the antibiotic cefaclor.
6) Literature
NH 2
O
H
N
O
Loracarbef
EC 3.5.1.11
● Zaks, A., Dodds, D.R. (1997) Application of biocatalysis and biotransformations to the synthesis
of pharmaceuticals, Drug Discovery Today 2, 513–530
● Zmijewski, M.J., Briggs, B.S., Thompson, A.R., Wright, I.G. (1991) Enantioselective acylation
of a beta-lactam intermediate in the synthesis of Loracarbef using penicillin G amidase, Tetrahedron
Lett. 32, 1621–1622
394
N
Cl
COOH