Industrial Biotransformations

Dehydrogenase
Candida sorbophila
N
1 = 1-pyridin-3-yl-ethanone
2 = 1-pyridin-3-yl-tosyl oxime
3 = 3-pyridyl-aminomethyl ketal
4 = amide-ketal
5 = pyridyl ketone
6 = aniline-alcohol
7 = 3-cyclopentyl-propionic acid
8 = (3-azido-propyl)-cyclopentane
9 = 4-amino-benzenesulfonic acid
10 = 4-isocyanato-benzenesulfonyl chloride
11 = sulfonyl chloride
12 = sulfonylamino-acetamide
13 = di-HCl salt
6) Literature
OH
Fig. 1.1.X.X – 2
H
N
O
O
N N
N N
NH
O
S
O
1. BH3 SMe2,
THF; 1 M H2SO4 2. purify via
phosphate salt,
then free base
75 %
EC 1.1.X.X
● Chartrain, M.M., Chung, J.Y.L., Roberge, C. (1998) N-(R)-(2-hydroxy-2-pyridine-3-yl-ethyl)-2-(4nitro-phenyl)-acetamide,
Merck & Co., Inc., US 5846791
● Chung, J.Y.L., Ho, G.-J., Chartrain, M., Roberge, C., Zhao, D., Leazer, J., Farr, R., Robbins, M.,
Emerson, K., Mathre, D.J., McNamara, J.M., Hughes, D.L., Grabowski, E.J.J., Reider, P.J.
(1999) Practical chemoenzymatic synthesis of a pyridylethanolamino beta-3 adrenergic receptor
agonist, Tetrahedron Lett. 40, 6739–6743
● Chartrain, M., Roberge, C., Chung, J., McNamara, J., Zhao, D., Olewinski, R., Hunt, G., Salmon,
P., Roush, D., Yamazaki, S., Wang, T., Grabowski, E., Buckland, B., Greasham, R. (1999)
Asymmetric bioreduction of (2-(4-nitro-phenyl)-N-(2-oxo-2-pyridin-3-yl-ethyl)-acetamide) to its
corresponding (R)-alcohol [(R)-N-(2-hydroxy-2-pyridin-3-yl-ethyl)-2-(4-nitro-phenyl)-acetamide]
by using Candida sorbophila MY 1833, Enzyme Microb. Technol. 25, 489–496
194
EtOH
HCl
92 %
N
2 HCl
OH
H
N
O
N N
N N
(R)-12 (R)-13
NH
O
S
O