Industrial Biotransformations

82
3 Retrosynthetic Biocatalysis
3.18
Sulfoxides and Sulfones
O
R S R'
O O
R S R'
oxygenase
chloroperoxidase
monooxygenase
R S R'
O
R S R'
Sulfoxides can be prepared from organic sulfur compounds by oxidation using monooxygenases
or chloroperoxidases; some of these are commercially available. Sulfones can
be produced from sulfoxides on slower further oxidation. When whole cells are used, a
mixture of two could be produced. The reversal of these types of reactions can also take
place under reductive conditions [56].
3.19
Halides
HO
R
R
X
O
O
X
NH2
R'
X
R R'''
R''
O
X
R R
Cl
N
H
X = Cl, Br, I
R
haloperoxidase
haloperoxidase
haloperoxidase
haloperoxidase
tryptophan
halogenase
R
R
O
R'
R R'''
R''
NH 2
O
N
H
+ H 2O 2 + X -
+ H2O2 + X -
R
+ H2O2 + X -
+ H 2O 2 + X -