Screening for new hydroxynitrilases from plants

Bioscience, Biotechnology and Biochemistry

Volumn 69, Issue 12, 2005, Pages 2349-2357

  Asano, Yasuhisa ^a   Tamura, Ken'ichirou ^a   Doi, Nobutaka ^a   Ueatrongchit, Techawaree ^b   H Kittikun, Aran ^b   Ohmiya, Tohru ^c  

^a TOYAMA PREFECTURAL UNIVERSITY   (Japan)

^b PRINCE OF SONGKLA UNIVERSITY   (Thailand)

^c Botanic Gardens of Toyama   (Japan)

Author keywords

Baliospermum montanum; Eriobotrya japonica; Hydroxynitrile lyase; Passiflora edulis; Prunus dulcis

Indexed keywords

BIOSYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KETONES; SEED;

BALIOSPERMUM MONTANUM; ERIOBOTRYA JAPONICA; HYDROXYNITRILE LYASE; PASSIFLORA EDULIS; PRUNUS DULCIS;

PLANTS (BOTANY);

2 PENTANONE; 2-PENTANONE; ACETONITRILE DERIVATIVE; ALKANONE; BENZALDEHYDE; BENZALDEHYDE DERIVATIVE; CYANOHYDRIN; HYDROLASE; ISOENZYME; MANDELONITRILE; NITRILASE; NITRILE; PLANT EXTRACT; POTASSIUM CYANIDE;

ARTICLE; CHEMISTRY; ENZYMOLOGY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; PLANT; PLANT SEED; PROTEIN CONFORMATION; PRUNUS; STEREOISOMERISM;

ACETONITRILES; AMINOHYDROLASES; BENZALDEHYDES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROGEN-ION CONCENTRATION; ISOENZYMES; MAGNETIC RESONANCE SPECTROSCOPY; NITRILES; PENTANONES; PLANT EXTRACTS; PLANTS; POTASSIUM CYANIDE; PROTEIN CONFORMATION; PRUNUS; SEEDS; STEREOISOMERISM;

BIOSYNTHESIS; KETONES; LIQUID CHROMATOGRAPHY; PLANTS; SEEDS;

ERIOBOTRYA JAPONICA; PASSIFLORA EDULIS; PRUNUS; PRUNUS DULCIS; PRUNUS MUME; PRUNUS PERSICA; SORBUS; SORBUS AUCUPARIA;

EID: 29344440805     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.69.2349     Document Type: Article

References (31)

1. Conn, E. E., Cyanogenic compounds. Annu. Rev. Plant Physiol., 31, 433-451 (1980).
2. Seigler, D. S., Cyanide and cyanogenic glycosides. In "Hervivores: Their Interactions with Secondary Plant Metabolites, 2nd Edition, Volume 1: The Chemical Participants", eds. Rosenthal, G. A., and Berenbaum, M. R., Academic Press, New York, pp. 35-77 (1991).
3. Lechtenberg, M., and Nahrstedt, A., Cyanogenic glycosides. In "Naturally Occurring Glycosides", ed. Ikan, R., John Wiley and Sons, West Sussex, pp. 147-191 (1999).
4. Effenberger, F., and Heid, S., (R)-Oxynitrilase catalyzed synthesis of (R)-ketone cyanohydrins. Tetrahedron: Asymmetry, 6, 2945-2952 (1995).
5. Becker, W., Benthin, U., Eschenhof, E., and Pfeil, E., Zur Kenntnis der Cyanhydrinsynthese II, Reindarstellung und Eigenshaften der Oxynitrtilase aus bittern Mandeln (Prunus communis Stokes). Biochem. Z., 337, 156-166 (1963).
6. Griengl, H., Klempier, N., Pöchlauer, P., Schmidt, M., Shi, N., and Zabelinskaya-Mackova, A. A., Enzyme catalyzed formation of (S)-cyanohydrins derived from aldehydes and ketones in a biphasic solvent system. Tetrahedron, 54, 14477-14486 (1998).
7. Asano, Y., Overview of screening for new microbial catalysts and their uses in organic synthesis: selection and optimization of biocatalysts. J. Biotechnol., 94, 65-72 (2002).
8. Wajant, H., and Förster, S., Purification and characterization of hydroxynitrile lyase from Hevea brasiliensis. Plant Sci., 115, 25-31 (1996).
9. White, W. L. B., Ariaz-Garzon, D. I., McMahon, J. M., and Sayre, R. T., Cyanogenesis in cassava: the role of hydroxynitrile lyase in root cyanide production. Plant Physiol., 116, 1219-1225 (1998).
10. Kuroki, G. W., and Conn, E. E., Mandelonitrile lyase from Ximenia americana L.: stereospecificity and lack of flavin prosthetic group. Proc. Natl. Acad. Sci. U.S.A., 86, 6978-6981 (1989).
11. Wajant, H., and Mundry, K. W., Hydroxynitrile lyase from Sorghum bicolor: a glycoprotein heterodimer. Plant Sci., 89, 127-133 (1993).
12. Hernández, L., Luna, H., Ruíz-Terán, F., and Vázquez, A., Screening for hydroxynitrile lyase activity in crude preparations of some edible plants. J. Mol. Cat. B: Enzymatic, 30, 105-108 (2004).
13. Bradford, M. M., A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem., 72, 248-254 (1976).
14. 2) and its application to gas chromatographic analysis of fatty acids. Chem. Pharm. Bull., 29, 1475-1478 (1981).
15. Effenberger, F., Hörsch, B., Weingart, F., Ziegler, T., and Kühner, S., Enzyme-catalyzed synthesis or (R)-ketone-cyanohydrins and their hydrolysis to (R)-α-hydroxy-α-methyl-carboxylic acids. Tetrahedron Lett., 32, 2605-2608 (1991).
16. Selmar, D., Carvalho, F. J. P., and Conn, E. E., A colorimetric assay for alpha-hydroxynitrile lyase. Anal. Biochem., 166, 208-211 (1987).
17. Gerstner, E., and Kiel, U., A new mandelonitrile lyase from the cherrylaurel (Prunus laurocerasus). Hoppe-Seylers Z. Physiol. Chem., 356, 1853-1857 (1975).
18. Yemm, R. S., and Poulton, J. E., Isolation and characterization of multiple forms of mandelonitrile lyase from mature black cherry (Prunus serotina Ehrh.) seeds. Arch. Biochem. Biophys., 247, 440-445 (1986).
19. Xu, L.-L., Singh, B. K., and Conn, E. E., Purification and characterization of mandelonitrile lyase from Prunus lyonii. Arch. Biochem. Biophys., 250, 322-328 (1986).
20. Bové, C., and Conn, E. E., Metabolism of aromatic compounds in higher plants. II. Purification and properties of the oxynitrilase of Sorghum vulgare. J. Biol. Chem., 236, 207-210 (1961).
21. Wajant, H., Mundry, K. W., and Pfizenmaier, K., Molecular cloning of hydroxynitrile lyase from Sorghum bicolor (L.). Homologies to serine carboxypeptidases. Plant Mol. Biol., 26, 735-746 (1994).
22. Xu, L.-L., Singh, B. K., and Conn, E. E., Purification and characterization of acetone cyanohydrin lyase from Linum usitatissimum. Arch. Biochem. Biophys., 263, 256-263 (1988).
23. Lauble, H., Mueller, K., Schindellin, H., Foerster, S., and Effenberger, F., Crystallization and preliminary X-ray diffraction studies of mandelonitrile lyase from almonds. Proteins, 19, 343-347 (1994).
24. Lauble, H., Knoedler, S., Schindelin, H., Foerster, S., Wajant, H., and Effenberger, F., Crystallographic studies and preliminary X-ray investigation of (S)-p-hydroxymandelonitrile lyase from Sorghum bicolor (L.). Acta Crystallogr. Sect. D, 52, 887-889 (1996).
25. Lauble, H., Decanniere, K., Wajant, H., and Effenberger, F., Crystallization and preliminary x-ray diffraction analysis of hydroxynitrile lyase from cassava (Manihot esculenta). Acta Crystallogr. Sect. D, 55, 904-906 (1999).
26. Wagner, U. G., Hasslacher, M., Griengl, H., Schwab, H., and Kratky, C., Mechanism of cyanogenesis: the crystal structure of hydroxynitrile lyase from Hevea brasiliensis. Structure, 4, 811-822 (1996).
27. Jorns, M. S., Solvent accessibility to flavin in oxynitrilase. Biochim. Biophys. Acta, 830, 30-35 (1985).
28. Chassagne, D., and Crouzet, J., A cyanogenic glycoside from Passiflora edulis fruits. Phytochemistry, 49, 757-759 (1998).
29. Mizutani, F., Yamada, M., Sugiura, A., and Tomana, T., The distribution of prunasin and amigdalin in Prunus species. Mem. Coll. Agric. Kyoto Univ., 113, 53-65 (1979).
30. Lin, G.-Q., Han, S.-Q., and Li, Z.-Y., Enzymatic synthesis of (R)-cyanohydrins by three (R)-oxynitrilase sources in micro-aqueous organic medium. Tetrahedron, 55, 3531-3540 (1999).
31. Nanda, S., Kato, Y., and Asano, Y., A new (R)-hydroxynitrile lyase from Prunus mume: asymmetric synthesis of cyanohydrins. Tetrahedron, 61, 10908-10916 (2005).