Page 290 - Cascade_Biocatalysis_Integrating_Stereoselective_and_Environmentally_Friendly_Reactions
P. 290
266 11 Nitrile Converting Enzymes Involved in Natural and Synthetic Cascade Reactions
Biodegradation potential of the genus pathways, persistent metabolites and
Rhodococcus. Environ. Int., 35, 162–177. involved degrader organisms. Environ.
12. Wang, D.X. and Wang, M.X. (2010) Pollut., 154, 155–168.
Biotransformations of three-membered 20. Holtze, M.S., Sorensen, J., Hansen,
(hetero) cyclic nitriles and their applica- H.C., and Aamand, J. (2006) Trans-
tions in organic synthesis. Prog. Chem., formation of the herbicide 2,6-
22, 1397–1402. dichlorobenzonitrile to the persistent
13. Leng, D.-H., Wang, D.-X., Pan, J., metabolite 2,6-dichlorobenzamide (BAM)
Huang, Z.-T., and Wang, M.-X. (2009) by soil bacteria known to harbour nitrile
Highly efficient and enantioselec- hydratase or nitrilase. Biodegradation, 17,
tive biotransformations of racemic 503–510.
azetidine-2-carbonitriles and their syn- 21. D’Antona, N., Nicolosi, G., Morrone, R.,
thetic applications. J. Org. Chem., 74, Kub´ ac, D., Kaplan, O., and Mart ´ ınkov´ a,
6077–6082. L. (2010) Synthesis of novel cyano-
14. Leng, D.-H., Wang, D.-X., Huang, Z.-T., cyclitols and their stereoselective bio-
and Wang, M.-X. (2010) Highly efficient transformation catalyzed by Rhodococcus
and enantioselective biotransformations erythropolis A4. Tetrahedron: Asymmetry,
of β-lactam carbonitriles and carboxam- 21, 695–702.
ides and their synthetic applications. 22. D’Antona, N., Morrone, R., Bovicelli,
Org. Biomol. Chem., 8, 4736–4743. P., Gambera, G., Kub´ aˇ c, D., and
15. Kinfe, H.H., Chhiba, V., Frederick, J., Mart ´ ınkov´ a, L. (2010) A novel chemo-
Bode, M.L., Mathiba, K., Steenkamp, multienzymatic synthesis of bioactive
P.A., and Brady, D. (2009) Enan- cyclophellitol and epi-cyclophellitol in
tioselective hydrolysis of β-hydroxy both enantiopure forms. Tetrahedron:
nitriles using the whole cell biocatalyst Asymmetry, 21, 2448–2454.
Rhodococcus rhodochrous ATCC BAA-870. 23. Kub´ aˇ c, D., ˇ Cejkov´ a, A., Mas´ ak, J., Jirku,
J. Mol. Catal. B: Enzym., 59, 231–236. V., Lemaire, M., Gallienne, E., Bolte,
16. Mylerov´ a, V. and Mart ´ ınkov´ a, L. J., Stloukal, R., and Mart ´ ınkov´ a, L.
(2003) Synthetic applications of nitrile- (2006) Biotransformation of nitriles by
converting enzymes. Curr. Org. Chem., Rhodococcus equi A4 immobilized in
7, 1279–1295. LentiKats ® . J. Mol. Catal. B: Enzym., 39,
17. Vesel´ a, A.B., Pelantov´ a, H., ˇ Sulc, M., 59–61.
Mackov´ a, M., Loveck´ a, P., Thimov´ a, 24. Kub´ aˇ c, D., Kaplan, O., Eliˇ s´ akov´ a, V.,
M., Pasquarelli, F., Piˇ cmanov´ a, M., P´ atek, M., Vejvoda, V., Sl´ amov´ a, K.,
P´ atek, M., Bhalla, T.C., and Mart ´ ınkov´ a, T´ othov´ a, A., Lemaire, M., Gallienne,
L. (2012) Biotransformation of ben- E., Lutz-Wahl, S., Fischer, L., Kuzma,
zonitrile herbicides via the nitrile M., Pelantov´ a, H., van Pelt, S., Bolte,
hydratase–amidase pathway in J., Kˇ ren, V., and Mart ´ ınkov´ a, L. (2008)
rhodococci. J. Ind. Microbiol. Biotechnol., Biotransformation of nitriles to amides
39, 1811–1819. using soluble and immobilized nitrile
18. Vesel´ a, A.B., Franc, M., Pelantov´ a, H., hydratase from Rhodococcus erythro-
Kub´ aˇ c, D., Vejvoda, V., ˇ Sulc, M., Bhalla, polis A4. J. Mol. Catal. B: Enzym., 50,
T.C., Mackov´ a, M., Loveck´ a, P., Jan ̊ u, 107–113.
P., Demnerov´ a, K., and Mart ´ ınkov´ a, 25. Cohen, M.A., Sawden, J., and Turner,
L. (2010) Hydrolysis of benzonitrile N.J. (1990) Selective hydrolysis of
herbicides by soil actinobacteria and nitriles under mild conditions by
metabolite toxicity. Biodegradation, 21, an enzyme. Tetrahedron Lett., 31,
761–770. 7223–7226.
19. Holtze, M.S., Sørensen, S.R., Sørensen, 26. Beard, T., Cohen, M.A., Parratt, J.S.,
J., and Aamand, J. (2008) Microbial Turner, N.J., Crosby, J., and Moilliet,
degradation of the benzonitrile her- J. (1993) Stereoselective hydrolysis of
bicides dichlobenil, bromoxynil and nitriles and amides under mild con-
ioxynil in soil and subsurface envi- ditions using a whole cell catalyst.
ronments – insights into degradation Tetrahedron: Asymmetry, 4, 1085–1104.