Chemo- and enantioselective hydrolysis of nitriles and acid amides, respectively, with resting cells of Rhodococcus sp. C3II and Rhodococcus erythropolis MP50

Journal of Biotechnology

Volumn 60, Issue 3, 1998, Pages 165-174

  Effenberger, Franz ^a   Graef, Bernd Walter ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Acid amide; Amidase; Nitrile; Nitrile hydratase; Regioselective hydrolysis; Rhodococcus

Indexed keywords

AROMATIC COMPOUNDS; BACTERIA; CATALYST ACTIVITY; CELLS; CYANIDES; DERIVATIVES; ENZYMES;

ACID AMIDE; ENANTIOSELECTIVE HYDROLYSIS; NITRILES; REGIOSELECTIVE HYDROLYSIS;

HYDROLYSIS;

AMIDE; IBUPROFEN; NAPROXEN; NITRILE;

ARTICLE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; RHODOCOCCUS; STEREOCHEMISTRY;

RHODOCOCCUS;

EID: 0345084461     PISSN: 01681656     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0168-1656(98)00004-2     Document Type: Article

References (47)

1. Asano Y., Fujishiro K., Tani Y., Yamada H. Microbial degradation of nitrile compounds. Part V. Aliphatic nitrile hydratase from Arthrobacter sp. J-1. Purification and characterization. Agric. Biol. Chem. 46:1982;1165-1174.
2. Bartling D., Seedorf M., Mithöfer A., Weiler E.W. Cloning and expression of an arabidopsis nitrilase which can convert indole-3-acetonitrile to the plant hormone, indole-3-acetic acid. Eur. J. Biochem. 205:1992;417-424.
3. Bengis-Garber C., Gutman A.L. Selective hydrolysis of dinitriles into cyano-carboxylic acids by Rhodococcus rhodochrous N.C.I.B.11216. Appl. Microbiol. Biotechnol. 32:1989;11-16.
4. Berther C. Einseitige Verseifung von Dinitrilen und Hydrierung der entstandenen ω-Cyan-Säureamide. Chem. Ber. 92:1959;2616-2621.
5. Bhalla T.C., Miura A., Wakamoto A., Ohba Y., Furuhashi K. Asymmetric hydrolysis of α-aminonitriles to optically active amino acids by a nitrilase of Rhodococcus rhodochrous PA-34. Appl. Microbiol. Biotechnol. 37:1992;184-190.
6. Böhme, J., 1993. Enzymatische Nitrilverseifung zu enantiomerenreinen α-Arylpropionsäuren. Dissertation, Universität Stuttgart.
7. Cohen M.A., Sawden J., Turner N.J. Selective hydrolysis of nitriles under mild conditions by an enzyme. Tetrahedron Lett. 31:1990;7223-7226.
8. Crosby J.A., Parratt J.S., Turner N.J. Enzymic hydrolysis of prochiral dinitriles. Tetrahedron: Asymmetry. 3:1992;1547-1550.
9. de Raadt A., Griengl H., Klempier N., Stütz A.E. A mild and simple enzymatic conversion of aldono- and aldurononitriles into the corresponding amides and/or carboxylic acids. J. Org. Chem. 58:1993;3179-3184.
10. Effenberger F., Böhme J. Enzyme-catalysed enantioselective hydrolysis of racemic naproxen nitrile. Bioorg. Med. Chem. 2:1994;715-721.
11. Effenberger F., Graef B.W., Oßwald S. Enzyme-catalyzed reactions, Part 30: Preparation of (S)-naproxen by enantioselective hydrolysis of racemic naproxen amide with resting cells of Rhodococcus erythropolis MP50 in organic solvents. Tetrahedron: Asymmetry. 8:1997;2749-2755.
12. Eliel E.L., Freeman J.P. Atrolactic acid. Org. Synth. Coll. 5:1963;58-62.
13. Fuson R.C., Emmons W.D., Tull R. The reaction of Grignard reagents with the cyanobenzoyldurenes. J. Org. Chem. 16:1951;648-654.
14. Gradley M.L., Knowles C.J. Asymmetric hydrolysis of chiral nitriles by Rhodococcus rhodochrous NCIMB 11216 nitrilase. Biotechnol. Lett. 16:1994;41-46.
15. Harper D.B. Characterization of a nitrilase from Nocardia sp. (Rhodochrous group) N.C.I.B. 11215, using p-hydroxybenzonitrile as sole carbon source. Int. J. Biochem. 17:1985;677-683.
16. Hashimoto Y., Nishiyama M., Horinouchi S., Beppu T. Nitrile hydratase gene from Rhodococcus sp. N-774. Requirement for its downstream region for efficient expression. Biosci. Biotechnol. Biochem. 58:1994;1859-1865.
17. Hjort C.M., Godtfredsen S.E., Emborg C. Isolation and characterization of a nitrile hydratase from a Rhodococcus sp. J. Chem. Tech. Biotechnol. 48:1990;217-226.
18. Hönicke-Schmidt, P., Schneider, M.P., 1990. Enzymatic hydrolysis of nitriles and dinitriles. J. Chem. Soc. Chem. Commun. 648-650.
19. Honda J., Kandori H., Okada T.et al. Spectroscopic observation of the intramolecular electron transfer in the photoactivation processes of nitrile hydratase. Biochemistry. 33:1994;3577-3583.
20. Hook R.H., Robinson W.G. Ricinine nitrilase II. Purification and properties. J. Biol. Chem. 239:1964;4263-4267.
21. Huisgen R., Axen C., Seidl H. Synthese oligomerer 1.3.4-Oxadiazolyl-m-phenyle. Chem. Ber. 98:1965;2966-2984.
22. Jin H., Turner I.M. Jr., Nelson M.J., Gurbiel R.J., Doan P.E., Hoffman B.M. Co-ordination sphere of the ferric ion in nitrile hydratase. J. Am. Chem. Soc. 115:1993;5290-5291.
23. Kakeya H., Sakai N., Sugai T., Ohta H. Microbial hydrolysis as a potent method for the preparation of optically active nitriles, amides and carboxylic acids. Tetrahedron Lett. 32:1991;1343-1346.
24. Kattwinkel P., Wolffenstein R. Über die Einwirkung von Persulfaten auf aromatische Nitrile. Ber. Dtsch. Chem. Ges. 37:1904;3221-3227.
25. Klempier N., de Raadt A., Faber K., Griengl H. Selective transformation of nitriles into amides and carboxylic acids by an immobilized nitrilase. Tetrahedron Lett. 32:1991;341-344.
26. Kobayashi M., Nagasawa T., Yamada H. Enzymic synthesis of acrylamide: a success story not yet over. Trends Biotechnol. 10:1992;402-408.
27. Kobayashi M., Komeda H., Nagasawa T.et al. Amidase coupled with low-molecular-mass nitrile hydratase from Rhodococcus rhodochrous J1 - sequencing and expression of the gene and purification and characterization of the gene product. Eur. J. Biochem. 217:1993;327-336.
28. Kurtz P. Untersuchungen über die Bildung von Nitrilen. Liebigs Ann. Chem. 572:1951;23-82.
29. Layh, N., 1994. Untersuchung nitrilhydrolysierender Enzymsysteme. Dissertation, Universität Stuttgart.
30. Layh N., Stolz A., Förster S., Effenberger F., Knackmuss H.-J. Enantioselective hydrolysis of O-acetylmandelonitrile to O-acetylmandelic acid by bacterial nitrilases. Arch. Microbiol. 158:1992;405-411.
31. Layh N., Stolz A., Böhme J., Effenberger F., Knackmuss H.-J. Enantioselective hydrolysis of racemic naproxen nitrile and naproxen amide to S-naproxen by new bacterial isolates. J. Biotechnol. 33:1994;175-182.
32. Levy-Schil S., Soubrier F., Crutz-Le Coq A.M., Faucher D., Crouzet J., Petre D. Aliphatic nitrilase from soil-isolated Comamonas testosteroni sp.: gene cloning and overexpression, purification and primary structure. Gene. 161:1995;15-20.
33. Levine M., Sedlecky R. Preparation of p- and m-aminomethylcyclohexylcarboxylic acid. J. Org. Chem. 24:1959;115-117.
34. Mahadevan S., Thimann K.V. Nitrilase II. Substrate specificity and possible mode of action. Arch. Biochem. Biophys. 107:1964;62-68.
35. Meth-Cohn, O., Wang, M.-X., 1997. Rationalisation of the regioselective hydrolysis of aliphatic dinitriles with Rhodococcus rhodochrous AJ270. Chem. Commun. 1041-1042.
36. Moreau J.L., Bigey F., Azza S., Arnaud A., Galzy P. The enzymatic production of adipic acid. Biocatalysis. 10:1994;325-340.
37. Nagasawa T., Nanba H., Ryuno K., Takeuchi K., Yamada H. Nitrile hydratase of Pseudomonas chlororaphis B23 - purification and characterization. Eur. J. Biochem. 162:1987;691-698.
38. Nagasawa T., Mauger J., Yamada H. A novel nitrilase, arylacetonitrilase, of Alcaligenes faecalis JM3 - purification and characterization. Eur. J. Biochem. 194:1990;765-772.
39. Nakao R., Oka K., Fukumoto T. A simple method for the esterification of carboxylic acids using chlorosilanes. Bull. Chem. Soc. Jpn. 54:1981;1267-1268.
40. Rieche A., Schön W. Luftoxydation von ε-Caprolactam und thermische Umwandlung der Oxydationsprodukte. Kunststoffe. 57:1967;49-52.
41. Robinson W.G., Hook R.H. Ricinine nitrilase I. Reaction product and substrate specificity. J. Biol. Chem. 239:1964;4257-4262.
42. Santaniello E., Ferraboschi P., Grisenti P., Manzocchi A. The biocatalytic approach to the preparation of enantiomerically pure chiral building blocks. Chem. Rev. 92:1992;1071-1140.
43. Shapiro S.L., Rose I.M., Roskin E., Freedman L. Pyridylethylated oxazolidinediones. II. J. Am. Chem. Soc. 81:1959;386-390.
44. Talley E.A., Fitzpatrick T.J., Porter W.L. Formation of fumaramic acid from asparagine in phosphate buffer. J. Am. Chem. Soc. 81:1959;174-175.
45. Warhurst A.M., Fewson C.A. Biotransformations catalyzed by the genus Rhodococcus. Crit. Rev. Biotechnol. 14:1994;29-73.
46. Yamamoto K., Fujimatsu I., Komatsu K. Purification and characterization of the nitrilase from Alcaligenes faecalis ATCC 8750 responsible for enantioselective hydrolysis of mandelonitrile. J. Ferment. Bioeng. 73:1992;425-430.
47. Yokoyama M., Sugai T., Ohta H. Asymmetric hydrolysis of a disubstituted malononitrile by the aid of a microorganism. Tetrahedron: Asymmetry. 4:1993;1081-1084.