Microbial synthesis and degradation of indole-3-acetic acid.  III.  Isolation and characterization of N-L-lysine

Hutzinger, O.; Kosuge, Takuo

doi:10.1021/bi00842a013

Cited by 67 publications

(37 citation statements)

References 19 publications

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“…The amount of IAA isolated was determined by UV spectrometry and by the Ehmann assay (8,21, and A. Ehmann, unpublished), and the amount of IAA in the tissue determined by isotope dilution (24). (13,18) and of IAA-amino acid conjugates (16,17) has been demonstrated and there is indirect evidence for enzymic hydrolysis of the esters (14). Presumably, the enzymes making and hydrolyzing the derivatives would be responsive to environmental inputs.…”

Section: Methodsmentioning

confidence: 99%

“…Other laboratories have reported the characterization of 1-0-(indole-3-acetyl)-3-D-glucose (31) and the peptide, indole-3-acetyl-N-aspartic acid formed from exogenous IAA (1) and as an endogenous compound (26). Indole-3-acetyl-e-L-lysine has been isolated from a Pseudomonad (17). Other IAA-sugar esters have been reported, as reviewed by Ehmann (6), but their identity has not been established.…”

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confidence: 99%

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Concentration of Indole-3-acetic Acid and Its Derivatives in Plants

Bandurski¹,

Schulze²

1977

Plant Physiol.

245

130

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Seeds of oat, coconut, soybean, sunflower, rice, millet, kidney bean, buckwheat, wheat, and corn and vegetative tissue of oit, pea, and corn were assayed for free indole-3-acetic acid (IAA), esterifled IAA, and peptidyl IAA. Three condusions were drwn: (a) al plat tissues examined contained most of their IAA as derivatives, either esterified or as a peptide; (b) the cereal grins examined contained mainly ester IAA; (c) the legume seeds examined contained mainly peptidyl IAA. Errors in analysis of free and bound IAA are dicsed.Previous studies from this laboratory have described the isolation and characterization of esters of IAA and myo-inositol, and of IAA and myo-inositol glycosides (cf. 19, 28) from Zea mays. The isolation of the 2-0, 4-0, and 6-0 esters of IAA and glucose (7) and esters having 2 or 3 mol of IAA/mol of inositol (9) have also been described. In (3,21) and an abstract of some of these data has appeared (25). This is the first attempt to assay simultaneously for free, ester and peptidyl IAA in a variety of plants.The validity of the isotope dilution method was established for IAA from Zea and Avena by demonstrating identity of the IAA by mass spectrometry and agreement in quantity when estimated by spectral, colorimetric, and gas chromatographic methods (3). Isotope dilution analysis of IAA has been accomplished earlier by Hamilton et al. (14) and by Belli et al. (4 Sunflower seed (Helianthus annuus), millet (Panicum miliaceum), buckwheat (Fagopyrum esculentum), and wheat (Triticum aestivum) were from a local health food store and gave 84, 23, 99, and 98% germination, respectively. Avena and Zea seed were as previously described (3, 21) and peas were from Vaughan's Seed Co., Ovid, Mich. Yeast (Saccharomyces cerevisiae) was a bakers' yeast from Anheuser Busch.Extraction. Vegetative tissue was extracted by homogenization in 70% acetone as previously described (3). The "4C-IAA and unlabeled, protective, indole-3-butyric acid were added immediately after homogenization. Yeast was treated as vegetative tissue except that 1,000 g were suspended in 1,700 ml of acetone to yield a final acetone concentration of 63%. Seeds were ground to a coarse powder in a hammer mill and samples of 300 g extracted for 10 hr in 2 liters of 70% acetone to which the "4C-IAA and indole-3-butyric acid had been added (3). The acetone extract was collected by filtration and the residue resuspended in 2 liters of 70% acetone and reextracted for 12 additional hr. Following filtration, the extracts were combined and reduced in volume (3).Hydrolysis and Extraction of IAA. Free IAA was extracted into ether from the acidified concentrated extract as described (3). Ester IAA was defined as IAA which was liberated by hydrolysis for 1 hr in 1 N NaOH at 22 to 25 C. Following hydrolysis the mixture was acidified and IAA plus hydrolyzed ester IAA were extracted into ether as described (3). Peptidic IAA was defined as IAA liberated during 3 hr of hydrolysis in 7 N NaOH at 100 C. For hydrolysis of peptidic IAA, the 70% acetone ...

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Concentration of Indole-3-acetic Acid and Its Derivatives in Plants

Bandurski¹,

Schulze²

1977

Plant Physiol.

245

130

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“…alek et al 1983}. Thus, the finding that IAA-lysine has 20--40% of the activity of IAA in A v e n a coleoptile bioassays is presumably due to hydrolysis of the conjugate to IAA (Hutzinger and Kosuge 1968a). Finally, structure/ function studies of various auxins also indicate that IAA-lysine should have little auxin activity [Thimann 1963}.…”

mentioning

confidence: 98%

“…In this study, the iaaL gene of Pseudomonas syringae subspecies savastanoi (P. savastanoi) was tested for anti-auxin activity in transgenic tobacco. The iaaL locus encodes an IAA-lysine synthetase activity that converts IAA to N*-indole -3-acetyl-L-lysine or IAA-lysine (Glass and Kosuge 1986;Hutzinger and Kosuge 1968b;Roberto et al 1990). Conjugation of IAA with aspartate or glutamate appears to play a crucial role in the inactivation and storage of endogenous IAA pools in plants (Cohen and Bialek 1984).…”

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confidence: 99%

Inactivation of auxin in tobacco transformed with the indoleacetic acid-lysine synthetase gene of Pseudomonas savastanoi.

Romano¹,

Hein²,

Klee³

1991

Genes Dev.

224

162

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“…Both JAM and IAA inhibit tryptophan oxidative decarboxylase. In addition IAA is further metabolized to indole-3-acetyl -L-lysine (IAA-lysine) (1)(2)(3).…”

mentioning

confidence: 99%

Factors Influencing the Production and Further Metabolism of Indole-3-Acetic Acid by Pseudomonas Savastanoi

Kuo

Kosuge

1969

J. Gen. Appl. Microbiol.

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Certain factors which affect production and accumulation of indole-3-acetic acid (IAA) and activity of enzymes associated with its synthesis from L-tryptophan were investigated in Pseudomonas savastanoi. Addition of Ltryptophan to the culture medium enhances the accumulation of IAA by the bacterium. However, both tryptophan oxidative decarboxylase and indoleacetamide hydrolase, which are involved in the conversion of L-tryptophan to IAA, are produced by the bacterium without addition of L-tryptophan to the medium. In a medium containing L-tryptophan, yields of tryptophan oxidative decarboxylase per liter of culture suspension were increased as much as 2-fold.IAA and indole-3-acetamide (JAM) strongly inhibit tryptophan oxidative decarboxylase. IAA up to 6 X 10-3 M did not inhibit indoleacetamide hydrolase. IAA also inhibits uptake of L-tryptophan by whole cells.IAA is converted to its lysine conjugate by the bacterium. During logarithmic phase of growth in a nutrient medium, the specific activities of tryptophan oxidative decarboxylase and indoleacetamide hydrolase were 2-fold greater than that for the system converting IAA to its lysine conjugate. During the stationary growth phase, specific activity of all three enzymes decreased but that for the first two enzymes did so more rapidly than the specific activity of the lysine conjugate synthetase. Accumulation of IAA in culture filtrates is controlled to a large extent by the relative activities of the systems synthesizing and utilizing IAA.Previous studies have shown that the bacterium, Pseudomonas savaslanoi converts L-tryptophan to indole-3-acetic acid (IAA) in two steps. In the first reaction catalyzed by tryptophan oxidative decarboxylase, L-tryptophan is converted to indole-3-acetamide (TAM). In the second reaction, catalyzed by

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Microbial synthesis and degradation of indole-3-acetic acid. III. Isolation and characterization of N-L-lysine

Cited by 67 publications

References 19 publications

Concentration of Indole-3-acetic Acid and Its Derivatives in Plants

Concentration of Indole-3-acetic Acid and Its Derivatives in Plants

Inactivation of auxin in tobacco transformed with the indoleacetic acid-lysine synthetase gene of Pseudomonas savastanoi.

Factors Influencing the Production and Further Metabolism of Indole-3-Acetic Acid by Pseudomonas Savastanoi

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