Industrial Biotransformations

Dehalogenase
Pseudomonas putida
5) Product application
● Applications include the synthesis of other optically active compounds such as pharmaceuticals.
● The main application of (S)-2-chloropropionic acid is in the synthesis of optically active phenoxypropionic
acid herbicides:
Fig. 3.8.1.2 – 3
Cl
Cl O COOH
Cl O COOH
EC 3.8.1.2
● Many of these herbicides were sold as racemates but because of environmental considerations,
the switch to the active enantiomer is preferred, thereby doubling capacities in existing plants
and leading to cost reduction through raw material savings.
● Other chiral products synthesized by this dehalogenase technique are shown in the following figure:
Cl
COOH
dichlorprop
CH3
N
F3C O O COOH
Cl
Br
O
N
COOH
fluazifop
mecoprop
O O COOH
fenoxaprop
OH
COOH
(S)-2-chloropropionic acid (S)-2-bromopropionic acid (S)-lactic acid
Br
OH
COOH
(S)-3-bromo-2-hydroxy-propionic acid
Fig. 3.8.1.2 – 4
Br
COOH
Br
OH
Br
COOH
COOH
(S)-2,3-dibromo-propionic acid
(S)-2-bromo-butyric acid (S)-2-hydroxy-butyric acid
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