Industrial Biotransformations

Transaminase
Bacillus megaterium
4) Process parameters
selectivity: 94 %
ee: > 99 %
reactor type: batch
enzyme consumption: 0.15 kgcatalyst powder ·kg –1 enzyme supplier:
product (t > 6 h)
Celgene Corporation, USA
company: Celgene Corporation, USA
5) Product application
● Possible products derived from (S)-methoxyisopropylamine are several agrochemicals, e. g.:
Fig. 2.6.1.X – 2
● Ciba spent about 10 years to find a chemical catalyst for the production of an enantiomerenriched
(S)-metolachlor. But only an ee of 79 % is possible resulting in a reduced application
rate of only 38 %. Other companies developed different approaches leading to higher product
costs than the biotransformation route.
6) Literature
N
O
O
Cl
EC 2.6.1.X
● Matcham, G.W. (1997) Chirality and biocatalysis in agrochemical production, INBIO Europe
97 Conference, Spring Innovations Ltd, Stockport, UK
● Matcham, G.W., Lee, S. (1994) Process for the preparation of chiral 1-aryl-2-aminopropanes,
Celgene Corporation, US 5,360,724
● Stirling, D.I., Matcham, G.W., Zeitlin, A.L. (1994) Enantiomeric enrichment and stereoselective
synthesis of chiral amines, Celgene Corporation, US 5,300,437
272
(S)-metolachlor (R)-metalaxyl
N
O
O
O
O