Primary or secondary? Versatile nitrilases in plant metabolism

Phytochemistry

Volumn 69, Issue 15, 2008, Pages 2655-2667

  Piotrowski, Markus ^a  

^a RUHR UNIVERSITY BOCHUM   (Germany)

Author keywords

Arabidopsis thaliana; Auxin biosynthesis; Cyanide detoxification; Cyanogenic glycosides; Glucosinolates; Nitrilase; Sorghum bicolor; Zea mays

Indexed keywords

HYDROLASE; NITRILASE;

CYTOLOGY; ENZYMOLOGY; GENETICS; METABOLISM; MOLECULAR CLONING; PHYLOGENY; PLANT; PROTEIN PROCESSING; PROTEIN TRANSPORT; REVIEW;

AMINOHYDROLASES; CLONING, MOLECULAR; PHYLOGENY; PLANTS; PROTEIN PROCESSING, POST-TRANSLATIONAL; PROTEIN TRANSPORT;

ARABIDOPSIS; ARABIDOPSIS THALIANA; BRASSICACEAE; SORGHUM BICOLOR; ZEA MAYS;

EID: 55049110692     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2008.08.020     Document Type: Review

References (146)

1. Akazawa T., Miljanich P., and Conn E.E. Studies on cyanogenic glycoside of Sorghum vulgare. Plant Physiol. 35 (1960) 535-538
2. Alexandersson E., Saalbach G., Larsson C., and Kjellbom P. Arabidopsis plasma membrane proteomics identifies components of transport, signal transduction and membrane trafficking. Plant Cell Physiol. 45 (2004) 1543-1556
3. Almeras E., Stolz S., Vollenweider S., Reymond P., Mene-Saffrane L., and Farmer E.E. Reactive electrophile species activate defense gene expression in Arabidopsis. Plant J. 34 (2003) 205-216
4. Andreasson E., Bolt J.L., Hoglund A.S., Rask L., and Meijer J. Different myrosinase and idioblast distribution in Arabidopsis and Brassica napus. Plant Physiol. 127 (2001) 1750-1763
5. Bak S., Paquette S.M., Morant M., Morant A.V., Saito S., Bjarnholt N., Zagrobelny M., Jørgensen K., Osmani S., Hamann T., Simonsen H.T., Pérez R.S., van Heeswijck T.B., Jørgensen B., and Møller B.L. Cyanogenic glycosides: a case study for evolution and application of cytochromes P450. Phytochem. Rev. 5 (2006) 309-329
6. Bak S., Tax F.E., Feldmann K.A., Galbraith D.W., and Feyereisen R. CYP83B1, a cytochrome P450 at the metabolic branch point in auxin and indole glucosinolate biosynthesis in Arabidopsis. Plant Cell 13 (2001) 101-111
7. Banerjee A., Sharma R., and Banerjee U.C. The nitrile-degrading enzymes: current status and future prospects. Appl. Microbiol. Biotechnol. 60 (2002) 33-44
8. Barlier I., Kowalczyk M., Marchant A., Ljung K., Bhalerao R., Bennett M., Sandberg G., and Bellini C. The SUR2 gene of Arabidopsis thaliana encodes the cytochrome P450 CYP83B1, a modulator of auxin homeostasis. Proc. Natl. Acad. Sci. USA 97 (2000) 14819-14824
9. Bartel B., and Fink G.R. Differential regulation of an auxin-producing nitrilase gene family in Arabidopsis thaliana. Proc. Natl. Acad. Sci. USA 91 (1994) 6649-6653
10. Bartling D., Seedorf M., Mithofer A., and 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
11. Bartling D., Seedorf M., Schmidt R.C., and Weiler E.W. Molecular characterization of two cloned nitrilases from Arabidopsis thaliana: key enzymes in biosynthesis of the plant hormone indole-3-acetic acid. Proc. Natl. Acad. Sci. USA 91 (1994) 6021-6025
12. Benschop J.J., Mohammed S., O'Flaherty M., Heck A.J., Slijper M., and Menke F.L. Quantitative phosphoproteomics of early elicitor signaling in Arabidopsis. Mol. Cell. Proteomics 6 (2007) 1198-1214
13. Bentley J.A., and Bickle A.S. Studies on plant growth hormones: II. Further biological properties of 3-indolacetonitrile. J. Exp. Bot 3 (1952) 406-423
14. Bentley J.A., and Housley S. Studies on Plant Growth Hormones: I. Biological activities of 3-indolacetaldehyde and 3-indolacetonitrile. J. Exp. Bot 3 (1952) 393-405
15. Bernardi R., Negri A., Ronchi S., and Palmieri S. Isolation of the epithiospecifier protein from oil-rape (Brassica napus ssp. oleifera) seed and its characterization. FEBS Lett 467 (2000) 296-298
16. Bestwick L.A., Gronning L.M., James D.C., Bones A., and Rossiter J.T. Purification and characterization of a nitrilase from Brassica napus. Physiol. Plant. 89 (1993) 811-816
17. Bischoff M., Low R., Grsic S., Rausch T., Hilgenberg W., and Ludwig-Müller J. Infection with the obligate biotroph Plasmodiophora brassicae, the causal agent of the clubroot disease, does not affect expression of NIT1/NIT2-related nitrilases in roots of Chinese cabbage. J. Plant Physiol. 147 (1995) 341-345
18. Bjarnholt N., and Møller B.L. Hydroxynitrile glucosides. Phytochemistry 69 (2008) 1947-1961
19. Bjarnholt N., Rook F., Motawia M.S., Cornett C., Jørgensen C., Olsen C.E., Jaroszewski J.W., Bak S., and Møller B.L. Diversification of an ancient theme: Hydroxynitrile glucosides. Phytochemistry 69 (2008) 1507-1516
20. Blumenthal S.G., Hendrickson H.R., Abrol Y.P., and Conn E.E. Cyanide metabolism in higher plants. III. The biosynthesis of β-cyanolanine. J. Biol. Chem. 243 (1968) 5302-5307
21. Blumenthal-Goldschmidt S., Butler G.W., and Conn E.E. Incorporation of hydrocyanic acid labelled with carbon-14 into asparagine in seedlings. Nature 197 (1963) 718-719
22. Bork P., and Koonin E.V. A new family of carbon-nitrogen hydrolases. Protein Sci. 3 (1994) 1344-1346
23. Brown P.D., Tokuhisa J.G., Reichelt M., and Gershenzon J. Variation of glucosinolate accumulation among different organs and developmental stages of Arabidopsis thaliana. Phytochemistry 62 (2003) 471-481
24. Burow M., Bergner A., Gershenzon J., and Wittstock U. Glucosinolate hydrolysis in Lepidium sativum - identification of the thiocyanate-forming protein. Plant Mol. Biol. 63 (2007) 49-61
25. Busk P.K., and Møller B.L. Dhurrin synthesis in sorghum is regulated at the transcriptional level and induced by nitrogen fertilization in older plants. Plant Physiol. 129 (2002) 1222-1231
26. Castric P.A., Farnden K.J., and Conn E.E. Cyanide metabolism in higher plants. V. The formation of asparagine from β-cyanoalanine. Arch. Biochem. Biophys. 152 (1972) 62-69
27. Chiba, R., Dohmoto, M., Yamaguchi, K., 1999. Oryza sativa (japonica cultivar-group) ONIT4 mRNA for nitrilase-like protein. GenBank Accession Number AB027054.
28. Cutler S.R., and Somerville C.R. Imaging plant cell death: GFP-Nit1 aggregation marks an early step of wound and herbicide induced cell death. BMC Plant Biol. 5 (2005) 4
29. 3-responsive genes in Arabidopsis thaliana by cDNA microarray analysis. Physiol. Plant. 128 (2006) 70-79
30. Dixon D.P., Skipsey M., Grundy N.M., and Edwards R. Stress-induced protein S-glutathionylation in Arabidopsis. Plant Physiol. 138 (2005) 2233-2244
31. Dohmoto M., Sano J., Isaji G., and Yamaguchi K. Indole acetonitrile-sensitivity of transgenic tobacco containing Arabidopsis thaliana nitrilase genes. Plant Cell Rep. 19 (2000) 1027-1032
32. Dohmoto M., Tsunoda H., Isaji G., Chiba R., and Yamaguchi K. Genes encoding nitrilase-like proteins from tobacco. DNA Res. 7 (2000) 283-289
33. Floss H.G., Hadwiger L., and Conn E.E. Enzymatic formation of β-cyanoalanine from cyanide. Nature 208 (1965) 1207-1208
34. Foo H.L., Gronning L.M., Goodenough L., Bones A.M., Danielsen B., Whiting D.A., and Rossiter J.T. Purification and characterisation of epithiospecifier protein from Brassica napus: enzymic intramolecular sulphur addition within alkenyl thiohydroximates derived from alkenyl glucosinolate hydrolysis. FEBS Lett. 468 (2000) 243-246
35. Force A., Lynch M., Pickett F.B., Amores A., Yan Y.L., and Postlethwait J. Preservation of duplicate genes by complementary, degenerative mutations. Genetics 151 (1999) 1531-1545
36. Forslund K., Morant M., Jørgensen B., Olsen C.E., Asamizu E., Sato S., Tabata S., and Bak S. Biosynthesis of the nitrile glucosides rhodiocyanoside A and D and the cyanogenic glucosides lotaustralin and linamarin in Lotus japonicus. Plant Physiol. 135 (2004) 71-84
37. Fowden L., and Bell E.A. Cyanide metabolism by seedlings. Nature 206 (1965) 110-112
38. Galaud J.P., Carriere M., Pauly N., Canut H., Chalon P., Caput D., and Pont-Lezica R.F. Construction of two ordered cDNA libraries enriched in genes encoding plasmalemma and tonoplast proteins from a high-efficiency expression library. Plant J. 17 (1999) 111-118
39. Galoian S.M., Tolosa E.A., and Goriachenkova E.V. Role of β-cyanoalanine hydratase in the synthesis of asparagine in white lupine. Biokhimiia. 47 (1982) 1949-1953
40. Giavalisco P., Nordhoff E., Kreitler T., Kloppel K.D., Lehrach H., Klose J., and Gobom J. Proteome analysis of Arabidopsis thaliana by two-dimensional gel electrophoresis and matrix-assisted laser desorption/ionisation-time of flight mass spectrometry. Proteomics 5 (2005) 1902-1913
41. Glawischnig E. Camalexin. Phytochemistry 68 (2007) 401-406
42. Grsic S., Kirchheim B., Pieper K., Fritsch M., Hilgenberg W., and Ludwig-Müller J. Induction of auxin biosynthetic enzymes by jasmonic acid and in clubroot diseased Chinese cabbage plants. Physiol. Plant. 105 (1999) 521-531
43. Grsic S., Sauerteig S., Neuhaus K., Albrecht M., Rossiter J., and Ludwig-Müller J. Physiological analysis of transgenic Arabidopsis thaliana plants expressing one nitrilase isoform in sense or antisense direction. J. Plant Physiol. 153 (1998) 446-456
44. Grsic-Rausch S., Kobelt P., Siemens J.M., Bischoff M., and Ludwig-Müller J. Expression and localization of nitrilase during symptom development of the clubroot disease in Arabidopsis. Plant Physiol. 122 (2000) 369-378
45. Halkier B.A., and Gershenzon J. Biology and biochemistry of glucosinolates. Annu. Rev. Plant Biol. 57 (2006) 303-333
46. Halkier B.A., and Møller B.L. Biosynthesis of the cyanogenic glucoside dhurrin in seedlings of Sorghum bicolor (L.) Moench and partial purification of the enzyme system involved. Plant Physiol 90 (1989) 1552-1559
47. Hendrickson H.R., and Conn E.E. Cyanide metabolism in higher plants. IV. Purification and properties of the β-cyanolanine synthase of blue lupine. J. Biol. Chem. 244 (1969) 2632-2640
48. Hillebrand H., Bartling D., and Weiler E.W. Structural analysis of the nit2/nit1/nit3 gene cluster encoding nitrilases, enzymes catalyzing the terminal activation step in indole-acetic acid biosynthesis in Arabidopsis thaliana. Plant Mol. Biol. 36 (1998) 89-99
49. Hillebrand H., Tiemann B., Hell R., Bartling D., and Weiler E.W. Structure of the gene encoding nitrilase 1 from Arabidopsis thaliana. Gene 170 (1996) 197-200
50. Hirai M.Y., Klein M., Fujikawa Y., Yano M., Goodenowe D.B., Yamazaki Y., Kanaya S., Nakamura Y., Kitayama M., Suzuki H., Sakurai N., Shibata D., Tokuhisa J., Reichelt M., Gershenzon J., Papenbrock J., and Saito K. Elucidation of gene-to-gene and metabolite-to-gene networks in Arabidopsis by integration of metabolomics and transcriptomics. J. Biol. Chem. 280 (2005) 25590-25595
51. Hogge L.R., Reed D.W., Underhill E.W., and Haughn G.W. HPLC separation of glucosinolates from leaves and seeds of Arabidopsis thaliana and their identification using thermospray liquid-chromatography mass-spectrometry. J. Chromatogr. Sci. 26 (1988) 551-556
52. Hook R.H., and Robinson W.G. Ricinine nitrilase. II. Purification and properties. J. Biol. Chem. 239 (1964) 4263-4267
53. Hung C.L., Liu J.H., Chiu W.C., Huang S.W., Hwang J.K., and Wang W.C. Crystal structure of Helicobacter pylori formamidase AmiF reveals a cysteine-glutamate-lysine catalytic triad. J. Biol. Chem. 282 (2007) 12220-12229
54. Husebye H., Chadchawan S., Winge P., Thangstad O.P., and Bones A.M. Guard cell- and phloem idioblast-specific expression of thioglucoside glucohydrolase 1 (myrosinase) in Arabidopsis. Plant Physiol. 128 (2002) 1180-1188
55. Ishikawa T., Okazaki K., Kuroda H., Itoh K., Mitsui T., and Hori H. Molecular cloning of Brassica rapa nitrilases and their expression during clubroot development. Mol. Plant Pathol. 8 (2007) 623-637
56. James D.C., and Rossiter J.T. Development and characteristics of myrosinase in Brassica napus during early seedling growth. Physiol. Plant. 82 (1991) 163-170
57. Jandhyala D., Berman M., Meyers P.R., Sewell B.T., Willson R.C., and Benedik M.J. CynD, the cyanide dihydratase from Bacillus pumilus: gene cloning and structural studies. Appl. Environ. Microbiol. 69 (2003) 4794-4805
58. Jandhyala D.M., Willson R.C., Sewell B.T., and Benedik M.J. Comparison of cyanide-degrading nitrilases. Appl. Microbiol. Biotechnol. 68 (2005) 327-335
59. Jenrich R., Trompetter I., Bak S., Olsen C.E., Møller B.L., and Piotrowski M. Evolution of heteromeric nitrilase complexes in Poaceae with new functions in nitrile metabolism. Proc. Natl. Acad. Sci. USA 104 (2007) 18848-18853
60. Jones E.R., Henbest H.B., Smith G.F., and Bentley J.A. 3-Indolylacetonitrile: a naturally occurring plant growth hormone. Nature 169 (1952) 485-487
61. Kimani S.W., Agarkar V.B., Cowan D.A., Sayed M.F., and Sewell B.T. Structure of an aliphatic amidase from Geobacillus pallidus RAPc8. Acta Crystallogr. D Biol. Crystallogr. 63 (2007) 1048-1058
62. Kobayashi M., Izui H., Nagasawa T., and Yamada H. Nitrilase in biosynthesis of the plant hormone indole-3-acetic acid from indole-3-acetonitrile: cloning of the Alcaligenes gene and site-directed mutagenesis of cysteine residues. Proc. Natl. Acad. Sci. USA 90 (1993) 247-251
63. Kobayashi M., Komeda H., Yanaka N., Nagasawa T., and Yamada H. Nitrilase from Rhodococcus rhodochrous J1. Sequencing and overexpression of the gene and identification of an essential cysteine residue. J. Biol. Chem. 267 (1992) 20746-20751
64. Kobayashi M., and Shimizu S. Nitrile hydrolases. Curr. Opin. Chem. Biol. 4 (2000) 95-102
65. Kobayashi M., Yanaka N., Nagasawa T., and Yamada H. Primary structure of an aliphatic nitrile-degrading enzyme, aliphatic nitrilase, from Rhodococcus rhodochrous K22 and expression of its gene and identification of its active site residue. Biochemistry 31 (1992) 9000-9007
66. Koroleva O.A., Davies A., Deeken R., Thorpe M.R., Tomos A.D., and Hedrich R. Identification of a new glucosinolate-rich cell type in Arabidopsis flower stalk. Plant Physiol. 124 (2000) 599-608
67. Kriechbaumer V., Park W.J., Piotrowski M., Meeley R.B., Gierl A., and Glawischnig E. Maize nitrilases have a dual role in auxin homeostasis and β-cyanoalanine hydrolysis. J. Exp. Bot. 58 (2007) 4225-4233
68. Kumaran D., Eswaramoorthy S., Gerchman S.E., Kycia H., Studier F.W., and Swaminathan S. Crystal structure of a putative CN hydrolase from yeast. Proteins 52 (2003) 283-291
69. Kutz A., Müller A., Hennig P., Kaiser W.M., Piotrowski M., and Weiler E.W. A role for nitrilase 3 in the regulation of root morphology in sulphur-starving Arabidopsis thaliana. Plant J. 30 (2002) 95-106
70. Lambrix V., Reichelt M., Mitchell-Olds T., Kliebenstein D.J., and Gershenzon J. The Arabidopsis epithiospecifier protein promotes the hydrolysis of glucosinolates to nitriles and influences Trichoplusia ni herbivory. Plant Cell 13 (2001) 2793-2807
71. Lea P.J., and Fowden L. Amino acid substrate specificity of asparaginyl-, aspartyl- and glutaminyl-tRNA synthetase isolated from higher plants. Phytochemistry 12 (1973) 1903-1916
72. Ljung K., Hull A.K., Kowalczyk M., Marchant A., Celenza J., Cohen J.D., and Sandberg G. Biosynthesis, conjugation, catabolism and homeostasis of indole-3-acetic acid in Arabidopsis thaliana. Plant Mol. Biol. 49 (2002) 249-272
73. Ludwig-Müller J., Pieper K., Ruppel M., Cohen J.D., Epstein E., Kiddle G., and Bennett R. Indole glucosinolate and auxin biosynthesis in Arabidopsis thaliana (L.) Heynh. glucosinolate mutants and the development of clubroot disease. Planta 208 (1999) 409-419
74. Lundgren S., Lohkamp B., Andersen B., Piskur J., and Dobritzsch D. The crystal structure of β-alanine synthase from Drosophila melanogaster reveals a homooctameric helical turn-like assembly. J. Mol. Biol. 377 (2008) 1544-1559
75. Mahadevan S., and Thimann K.V. Nitrilase. II. Substrate specificity and possible mode of action. Arch. Biochem. Biophys. 107 (1964) 62-68
76. McBride K.E., Kenny J.W., and Stalker D.M. Metabolism of the herbicide bromoxynil by Klebsiella pneumoniae subsp. Ozaenae. Appl. Environ. Microbiol. 52 (1986) 325-330
77. Morant A.V., Bjarnholt N., Kragh M.E., Kjaergaard C.H., Jørgensen K., Paquette S.M., Piotrowski M., Imberty A., Olsen C.E., Møller B.L., and Bak S. The β-glucosidases responsible for bioactivation of hydroxynitrile glucosides in Lotus japonicus. Plant Physiol. 147 (2008) 1072-1091
78. Morant A.V., Jørgensen K., Jørgensen C., Paquette S.M., Sanchez-Perez R., Møller B.L., and Bak S. Β-Glucosidases as detonators of plant chemical defense. Phytochemistry 69 (2008) 1795-1813
79. Müller A., and Weiler E.W. Indolic constituents and indole-3-acetic acid biosynthesis in the wild-type and a tryptophan auxotroph mutant of Arabidopsis thaliana. Planta 211 (2000) 855-863
80. Nafisi M., Goregaoker S., Botanga C.J., Glawischnig E., Olsen C.E., Halkier B.A., and Glazebrook J. Arabidopsis cytochrome P450 monooxygenase 71A13 catalyzes the conversion of indole-3-acetaldoxime in camalexin synthesis. Plant Cell 19 (2007) 2039-2052
81. Nagasawa T., Wieser M., Nakamura T., Iwahara H., Yoshida T., and Gekko K. Nitrilase of Rhodococcus rhodochrous J1. Conversion into the active form by subunit association. Eur. J. Biochem. 267 (2000) 138-144
82. Nakai T., Hasegawa T., Yamashita E., Yamamoto M., Kumasaka T., Ueki T., Nanba H., Ikenaka Y., Takahashi S., Sato M., and Tsukihara T. Crystal structure of N-carbamyl-d-amino acid amidohydrolase with a novel catalytic framework common to amidohydrolases. Structure 8 (2000) 729-737
83. Neuhaus K., Grsic-Rausch S., Sauerteig S., and Ludwig-Müller J. Arabidopsis plants transformed with nitrilase 1 or 2 in antisense direction are delayed in clubroot development. J. Plant Physiol. 156 (2000) 756-761
84. Nikiforova V., Freitag J., Kempa S., Adamik M., Hesse H., and Hoefgen R. Transcriptome analysis of sulfur depletion in Arabidopsis thaliana: interlacing of biosynthetic pathways provides response specificity. Plant J. 33 (2003) 633-650
85. Normanly J., Cohen J.D., and Fink G.R. Arabidopsis thaliana auxotrophs reveal a tryptophan-independent biosynthetic pathway for indole-3-acetic acid. Proc. Natl. Acad. Sci. USA 90 (1993) 10355-10359
86. Normanly J., Grisafi P., Fink G.R., and Bartel B. Arabidopsis mutants resistant to the auxin effects of indole-3-acetonitrile are defective in the nitrilase encoded by the NIT1 gene. Plant Cell 9 (1997) 1781-1790
87. O'Donnell P.J., Schmelz E.A., Moussatche P., Lund S.T., Jones J.B., and Klee H.J. Susceptible to intolerance - a range of hormonal actions in a susceptible Arabidopsis pathogen response. Plant J. 33 (2003) 245-257
88. O'Reilly C., and Turner P.D. The nitrilase family of CN hydrolysing enzymes - a comparative study. J. Appl. Microbiol. 95 (2003) 1161-1174
89. Osswald S., Wajant H., and Effenberger F. Characterization and synthetic applications of recombinant AtNIT1 from Arabidopsis thaliana. Eur. J. Biochem. 269 (2002) 680-687
90. Pace H.C., and Brenner C. The nitrilase superfamily: classification, structure and function. Genome Biol. 2 (2001) (REVIEWS0001)
91. Pace H.C., Hodawadekar S.C., Draganescu A., Huang J., Bieganowski P., Pekarsky Y., Croce C.M., and Brenner C. Crystal structure of the worm NitFhit Rosetta Stone protein reveals a Nit tetramer binding two Fhit dimers. Curr. Biol. 10 (2000) 907-917
92. Park W.J., Kriechbaumer V., Müller A., Piotrowski M., Meeley R.B., Gierl A., and Glawischnig E. The nitrilase ZmNIT2 converts indole-3-acetonitrile to indole-3-acetic acid. Plant Physiol. 133 (2003) 794-802
93. Paterson A.H., Bowers J.E., and Chapman B.A. Ancient polyploidization predating divergence of the cereals, and its consequences for comparative genomics. Proc. Natl. Acad. Sci. USA 101 (2004) 9903-9908
94. Peiser G.D., Wang T.-T., Hoffman N.E., Yang S.F., Liu H.-W., and Walsh C.T. Formation of cyanide from carbon 1 of 1-aminocyclopropane-1-carboxylic acid during its conversion to ehtylene. Proc. Natl. Acad. Sci. USA 81 (1984) 3059-3063
95. Petersen B.L., Chen S., Hansen C.H., Olsen C.E., and Halkier B.A. Composition and content of glucosinolates in developing Arabidopsis thaliana. Planta 214 (2002) 562-571
96. Piotrowski M., Janowitz T., and Kneifel H. Plant C-N hydrolases and the identification of a plant N-carbamoylputrescine amidohydrolase involved in polyamine biosynthesis. J. Biol. Chem. 278 (2003) 1708-1712
97. Piotrowski M., Schönfelder S., and Weiler E.W. The Arabidopsis thaliana isogene NIT4 and its orthologs in tobacco encode β-cyano-l-alanine hydratase/nitrilase. J. Biol. Chem. 276 (2001) 2616-2621
98. Piotrowski M., and Volmer J.J. Cyanide metabolism in higher plants: cyanoalanine hydratase is a NIT4 homolog. Plant Mol. Biol. 61 (2006) 111-122
99. Pirrung M.C. Ethylene biosynthesis. 3. Evidence concerning the fate of C1-N1 of 1-aminocyclopropane carboxylic-acid. Bioorgan. Chem 13 (1985) 219-226
100. Pollmann S., Müller A., Piotrowski M., and Weiler E.W. Occurrence and formation of indole-3-acetamide in Arabidopsis thaliana. Planta 216 (2002) 155-161
101. Pollmann S., Müller A., and Weiler E.W. Many roads lead to "auxin": of nitrilases, synthases, and amidases. Plant Biol. 8 (2006) 326-333
102. Poole R.J., and Thimann K.V. Uptake of indole-3-acetic acid and indole-3-acetonitrile by Avena coleoptile sections. Plant Physiol. 39 (1964) 98-103
103. Purkarthofer T., Skranc W., Schuster C., and Griengl H. Potential and capabilities of hydroxynitrile lyases as biocatalysts in the chemical industry. Appl. Microbiol. Biotechnol. 76 (2007) 309-320
104. Rausch T., Butcher D.N., and Hilgenberg W. Nitrilase activity in clubroot diseased plants. Physiol. Plant. 52 (1981) 467-470
105. Rausch T., and Hilgenberg W. Partial purification of nitrilase from Chinese Cabbage. Phytochemistry 19 (1980) 747-750
106. Reintanz B., Lehnen M., Reichelt M., Gershenzon J., Kowalczyk M., Sandberg G., Godde M., Uhl R., and Palme K. Bus, a bushy Arabidopsis CYP79F1 knockout mutant with abolished synthesis of short-chain aliphatic glucosinolates. Plant Cell 13 (2001) 351-367
107. Ressler C. Isolation and identification from common vetch of neurotoxin β-cyano-l-alanine, a possible factor in neurolathyrism. J. Biol. Chem. 237 (1962) 733-735
108. Ressler C., Giza Y.H., and Nigam S.N. Biosynthesis and metabolism in species of vetch and Lathyrus of γ-glutamyl-β-cyanoalanine: Relation to the biosynthesis of asparagine. J. Am. Chem. Soc. 85 (1963) 2874-2875
109. Robinson W.G., and Hook R.H. Ricinine nitrilase. I. Reaction product and substrate specificity. J. Biol. Chem. 239 (1964) 4257-4262
110. Rosenthaler L. Durch Enzyme bewirkte asymmetrische Synthesen. Biochem. Z. 14 (1908) 238-253
111. Sakai N., Tajika Y., Yao M., Watanabe N., and Tanaka I. Crystal structure of hypothetical protein PH0642 from Pyrococcus horikoshii at 1.6Å resolution. Proteins 57 (2004) 869-873
112. Sanchez-Perez R., Jørgensen K., Olsen C.E., Dicenta F., and Møller B.L. Bitterness in almonds. Plant Physiol. 146 (2008) 1040-1052
113. Sarry J.E., Kuhn L., Le Lay P., Garin J., and Bourguignon J. Dynamics of Arabidopsis thaliana soluble proteome in response to different nutrient culture conditions. Electrophoresis 27 (2006) 495-507
114. Schmidt R.C., Müller A., Hain R., Bartling D., and Weiler E.W. Transgenic tobacco plants expressing the Arabidopsis thaliana nitrilase II enzyme. Plant J. 9 (1996) 683-691
115. Schranz M.E., and Mitchell-Olds T. Independent ancient polyploidy events in the sister families Brassicaceae and Cleomaceae. Plant Cell 18 (2006) 1152-1165
116. Sewell B.T., Berman M.N., Meyers P.R., Jandhyala D., and Benedik M.J. The cyanide degrading nitrilase from Pseudomonas stutzeri AK61 is a two-fold symmetric, 14-subunit spiral. Structure 11 (2003) 1413-1422
117. Shimaoka T., Ohnishi M., Sazuka T., Mitsuhashi N., Hara-Nishimura I., Shimazaki K., Maeshima M., Yokota A., Tomizawa K., and Mimura T. Isolation of intact vacuoles and proteomic analysis of tonoplast from suspension-cultured cells of Arabidopsis thaliana. Plant Cell Physiol. 45 (2004) 672-683
118. Siemens J., Glawischnig E., and Ludwig-Müller J. Indole glucosinolates and camalexin do not influence the development of the clubroot disease in Arabidopsis thaliana. J. Phytopathol. 156 (2008) 332-337
119. Stalker D.M., Malyj L.D., and McBride K.E. Purification and properties of a nitrilase specific for the herbicide bromoxynil and corresponding nucleotide sequence analysis of the bxn gene. J. Biol. Chem. 263 (1988) 6310-6314
120. Stalker D.M., and McBride K.E. Cloning and expression in Escherichia coli of a Klebsiella ozaenae plasmid-borne gene encoding a nitrilase specific for the herbicide bromoxynil. J. Bacteriol. 169 (1987) 955-960
121. Stalker D.M., McBride K.E., and Malyj L.D. Herbicide resistance in transgenic plants expressing a bacterial detoxification gene. Science 242 (1988) 419-423
122. Steiner M. Ein Beitrag zur Konstitutionsspezifität der Heteroauxinwirkung. Planta 36 (1948) 131-153
123. Stevenson D.E., Feng R., and Storer A.C. Detection of covalent enzyme-substrate complexes of nitrilase by ion-spray mass spectroscopy. FEBS Lett. 277 (1990) 112-114
124. Stintzi A., Weber H., Reymond P., Browse J., and Farmer E.E. Plant defense in the absence of jasmonic acid: the role of cyclopentenones. Proc. Natl. Acad. Sci. USA 98 (2001) 12837-12842
125. Stowe B.B., and Thimann K.V. The paper chromatography of indole compounds and some indole-containing auxins of plant tissues. Arch. Biochem. 51 (1954) 499-516
126. Thimann K.V. Hydrolysis of indoleacetonitrile in plants. Arch. Biochem. Biophys. 44 (1953) 242-243
127. Thimann K.V., and Mahadevan S. Enzymatic hydrolysis of indoleacetonitrile. Nature 181 (1958) 1466-1467
128. Thimann K.V., and Mahadevan S. Nitrilase. I. Occurrence, preparation, and general properties of the enzyme. Arch. Biochem. Biophys 105 (1964) 133-141
129. Thuku R.N., Weber B.W., Varsani A., and Sewell B.T. Post-translational cleavage of recombinantly expressed nitrilase from Rhodococcus rhodochrous J1 yields a stable, active helical form. FEBS J. 274 (2007) 2099-2108
130. 14CN by Lathyrus odoratus L., Vicia sativa L., and Ricinus communis L. Phytochemistry 3 (1964) 365-367
131. Tsunoda H., and Yamaguchi K. The cDNA sequence of an auxin-producing nitrilase homolog in tobacco. Plant Physiol 109 (1995) 339
132. Vorwerk S., Biernacki S., Hillebrand H., Janzik I., Müller A., Weiler E.W., and Piotrowski M. Enzymatic characterization of the recombinant Arabidopsis thaliana nitrilase subfamily encoded by the NIT2/NIT1/NIT3-gene cluster. Planta 212 (2001) 508-516
133. Wajant H., and Effenberger F. Hydroxynitrile lyases of higher plants. Biol. Chem. 377 (1996) 611-617
134. Wang W.C., Hsu W.H., Chien F.T., and Chen C.Y. Crystal structure and site-directed mutagenesis studies of N-carbamoyl-d-amino-acid amidohydrolase from Agrobacterium radiobacter reveals a homotetramer and insight into a catalytic cleft. J. Mol. Biol. 306 (2001) 251-261
135. Watanabe M., Kusano M., Oikawa A., Fukushima A., Noji M., and Saito K. Physiological roles of the β-substituted alanine synthase gene family in Arabidopsis. Plant Physiol. 146 (2008) 310-320
136. Weber H., Chetelat A., Reymond P., and Farmer E.E. Selective and powerful stress gene expression in Arabidopsis in response to malondialdehyde. Plant J. 37 (2004) 877-888
137. Wienkoop S., Zoeller D., Ebert B., Simon-Rosin U., Fisahn J., Glinski M., and Weckwerth W. Cell-specific protein profiling in Arabidopsis thaliana trichomes: identification of trichome-located proteins involved in sulfur metabolism and detoxification. Phytochemistry 65 (2004) 1641-1649
138. Woodward A.W., and Bartel B. Auxin: regulation, action, and interaction. Ann. Bot. (Lond) 95 (2005) 707-735
139. Xie Z.Y., Feng J.L., Garcia E., Bernett M., Yazbeck D., and Tao J.H. Cloning and optimization of a nitrilase for the synthesis of (3S)-3-cyano-5-methyl hexanoic acid. J. Mol. Catal. B - Enzym. 41 (2006) 75-80
140. Xu P., Narasimhan M.L., Samson T., Coca M.A., Huh G.H., Zhou J., Martin G.B., Hasegawa P.M., and Bressan R.A. A nitrilase-like protein interacts with GCC box DNA-binding proteins involved in ethylene and defense responses. Plant Physiol. 118 (1998) 867-874
141. Yamada H., Shimizu S., and Kobayashi M. Hydratases involved in nitrile conversion: screening, characterization and application. Chem. Rec. 1 (2001) 152-161
142. Zagrobelny M., Bak S., and Møller B.L. Cyanogenesis in plants and arthropods. Phytochemistry 69 (2008) 1457-1468
143. Zhang Z., Ober J.A., and Kliebenstein D.J. The gene controlling the quantitative trait locus EPITHIOSPECIFIER MODIFIER1 alters glucosinolate hydrolysis and insect resistance in Arabidopsis. Plant Cell 18 (2006) 1524-1536
144. Zhao Y., Hull A.K., Gupta N.R., Goss K.A., Alonso J., Ecker J.R., Normanly J., Chory J., and Celenza J.L. Trp-dependent auxin biosynthesis in Arabidopsis: involvement of cytochrome P450s CYP79B2 and CYP79B3. Genes Dev. 16 (2002) 3100-3112
145. Zimmerman P.W., and Wilcoxon F. Several chemical growth substances which cause initiation of roots and other responses in plants. Contrib. Boyce Thompson Inst. 7 (1935) 209-229
146. Zybailov B., Rutschow H., Friso G., Rudella A., Emanuelsson O., Sun Q., and van Wijk K.J. Sorting signals, N-terminal modifications and abundance of the chloroplast proteome. PLoS ONE. 3 (2008) e1994