Page 330 - Cascade_Biocatalysis_Integrating_Stereoselective_and_Environmentally_Friendly_Reactions

306 14 Enzymatic Stereoselective Synthesis of -Amino Acids

Table 14.2 Enantioselective conversion of racemic β-aminonitriles.

Substrate Functional groups Reaction catalyzed Selectivity Organism

NHR R-C H CO- Hydrolysis of cyclic 99% ee (nitrile) Rhodococcus equi A4 [62]
5
6
β-aminonitriles >95% ee (acid)
CN
44% ee (nitrile) R. erythropolis NCIMB
>95% ee (acid) 11540 [62]
82% ee (nitrile) Rhodococcus sp. R312 [62]
>95% ee (acid)
R-p-CH C H SO - Hydrolysis of cyclic 78% ee (nitrile) Rhodococcus equi A4 [62]
2
4
3 6
β-aminonitriles >99% ee (acid)
98% ee (nitrile) 97% R. erythropolis NCIMB
ee (acid) 11540 [62]
47% ee (nitrile) 87% Rhodococcus sp. R312 [62]
ee (acid)
NHR R=C H CO- Hydrolysis of cyclic 94% ee (amide) Rhodococcus equi A4 [62]
6 5
β-aminonitriles
CN
>99% ee (amide) Rhodococcus erythropolis
NCIMB 11540 [62]
>99% ee (amide) Rhodococcus sp. R312 [62]
R=p-CH C H SO - Hydrolysis of cyclic >99% ee (amide) Rhodococcus equi A4 [62]
3 6 4 2
β-aminonitriles
>99% ee (amide) Rhodococcus erythropolis
NCIMB 11540 [62]
>99% ee (amide) Rhodococcus sp. R312 [62]
1
NHR R-benzyl R -ethyl Hydrolysis of >99.5% ee (amide) Rhodococcus erythropolis AJ
aliphatic >99.5% ee (acid) 270 [1]
R 1 CN β-aminonitriles
R-benzyl Hydrolysis of >99.5% ee (amide) Rhodococcus erythropolis AJ
1
R -isopropyl aliphatic 90.2% ee (acid) 270 [1]
β-aminonitriles
R-benzyl Hydrolysis of 92.4% ee (amide) Rhodococcus erythropolis AJ
1
R -cyclopropyl aliphatic 96.4% ee (acid) 270 [1]
β-aminonitriles
1
R-benzyl R -methyl Hydrolysis of 74.2% (amide) 86.6% Rhodococcus erythropolis AJ
aliphatic ee (acid) 270 [1]
β-aminonitriles
1
R-H R -4-methoxy Hydrolysis of 85% ee ((S)-nitrile) Rhodococcus rhodochrous
phenyl aliphatic 62% ee ((R)-amide) BAA-870 [12]
β-aminonitriles