Separation and Properties of Argininosuccinate and Its Two Anhydrides and Their Detection in Biological Materials<sup>*</sup>

Ratner, S.; Kunkemueller, Mary

doi:10.1021/bi00870a007

Cited by 42 publications

(19 citation statements)

References 18 publications

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“…Evidence for diminished canavanine formation from ureidohomoserine, due to canavaninosuccinic acid loss via anhydride or other derivative formation, was not obtained. This loss is known to occur with argininosuccinic acid (10). The appreciable time-dependent diminution in the label contained within canavanine and arginine is consistent with their role in providing nitrogen for the developing plant.…”

Section: Resultsmentioning

confidence: 59%

l-Canavanine Metabolism in Jack Bean, Canavalia ensiformis (L.) DC. (Leguminosae)

Rosenthal¹

1982

Plant Physiol.

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L-Canavanine, a highly toxic arginine antimetabolite, is the principal nonprotein amino acid of many eguminous plants. Labeled-precursor feeding studies, conducted primarily with I'Clcarbamoyl sphate, and utilization of the seedlins of jack bean, Canavalia enuiformis (L.) DC. (Leguminosae), have provided evidence for L-canavanine biosynthesis from L-canaline via O-ureido-L-homoserine. This reaction pathway appears to constitute an important in vivo route ofcanavanine productiol Canavanine cleavage to canaline may represent a degradative phase of canavanine metabolism distinct from the anabolic reactions described above. Thus, while these reactions of canavanine metabolism bear analgy to the mammalian Krebs-Henseleit ornithie-urea cycle, no evidence has been obtained at present for the reutilization of canaline in ureidohonoserine formation.L-Canavanine, a nonprotein amino acid found in at least 500 species of leguminous plants (2), is a potent antimetabolite, due in large measure to its structural analogy to L-arginine. Canavanine's marked insecticidal action, its ability to disrupt many essential biochemical reactions in a wide range of prokaryotic and eukaryotic organisms, and its appreciable storage in such important tissues as the seed are consistent with its allelochemical role in plant defense against phytophagous insects and other herbivores (14).Canavanine is a major nitrogen storage metabolite of the seed, where it can account for 95% or more of the nitrogen found in the free amino acids (15). Its mobilization and utilization injack bean, Canavalia ens!formis (L.) DC. (Leguminosae), occurs via arginase (EC 3.5.3.1), which cleaves L-canavanine to L-canaline and urea (3). Urea is hydrolyzed by urease (EC 3.5.1.5) to CO2 and NH3; the latter, representing an important source of reduced nitrogen, is assimilated and incorporated into the amide nitrogen of asparagine (I 1).Experimental evidence has been obtained in jack bean for carbamylation ofcanaline with carbamoyl phosphate, in a reaction catalyzed by ornithine carbamoyltransferase (EC 2.1.3.3) to yield O-ureido-L-homoserine, a citrulline analog (12). Argininosuccinic acid lyase (EC 4.3.2.1), the enzyme-mediating conversion of Lcanavaninosuccinic acid to L-canavanine and fumaric acid, has been isolated and purified extensively from jack bean seed (16). Of the reactions depicted in Figure 1, it is the reaction fostered by argininosuccinic acid synthetase (EC 6.3 The enzymic reactions of the nonprotein amino acids depicted in Figure 1 result in a reaction pathway that bears similarity to mammalian urea production via the Krebs-Henseleit ornithineurea cycle. All of the ornithine-urea cycle enzymes have been isolated from several higher plants, including jack bean (18). Attempts have been made to isolate an enzyme responsible for the formation of one of the intermediates of canavanine metabolism that is distinct from its ornithine-urea cycle counterpart. These efforts have failed (3,9).One can readily demonstrate all of the ornithine-urea cycle e...

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Section: Resultsmentioning

confidence: 59%

l-Canavanine Metabolism in Jack Bean, Canavalia ensiformis (L.) DC. (Leguminosae)

Rosenthal¹

1982

Plant Physiol.

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“…A specimen of hair was hydrolysed in a sealed tube with 6N-hydrochloric acid and the resultant amino acids examined by 2-dimensional electrophoresis and chromatography. There was no trace of argininosuccinic acid or of its cyclic anhydrides (Westall, 1960;Ratner and Kunkemueller, 1966). It was noticed, however, that the proportions of the amino acids were different from those from a sample of normal hair so treated.…”

mentioning

confidence: 88%

Sibs with mental and physical retardation and trichorrhexis nodosa with abnormal amino acid composition of the hair.

Pollitt¹,

Jenner²,

Davies³

1968

Archives of Disease in Childhood

139

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“…The rate increases with increases in acidity and temperature. Anhydride I can be hydrolyzed by raising the pH, but not anhydride 11 (139,140). Anhydride I1 is formed from argininosuccinate more slowly than anhydride I.…”

Section: Interconversions Between Argininosuccinate and Its Two Anhydmentioning

confidence: 99%

“…Differences between the anhydrides bearing on structure are (a) greater heat lability of anhydride I, (b) a higher dissociation constant for the guanidino anhydride grouping of anhydride I, (c) an absorption maximum shown by anhydride I1 in the short ultraviolet region but not shown by anhydride I (188,139) and ( d ) ease of oxidation of anhydride I.…”

Section: Properties and Structures Of Anhydrides Z And Zzmentioning

confidence: 99%

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Enzymes of Arginine and Urea Systhesis

Ratner¹

1973

Advances in Enzymology - And Related Areas of Molecular Biology

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Separation and Properties of Argininosuccinate and Its Two Anhydrides and Their Detection in Biological Materials^*

Cited by 42 publications

References 18 publications

l-Canavanine Metabolism in Jack Bean, Canavalia ensiformis (L.) DC. (Leguminosae)

l-Canavanine Metabolism in Jack Bean, Canavalia ensiformis (L.) DC. (Leguminosae)

Sibs with mental and physical retardation and trichorrhexis nodosa with abnormal amino acid composition of the hair.

Enzymes of Arginine and Urea Systhesis

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Separation and Properties of Argininosuccinate and Its Two Anhydrides and Their Detection in Biological Materials*

Cited by 42 publications

References 18 publications

l-Canavanine Metabolism in Jack Bean, Canavalia ensiformis (L.) DC. (Leguminosae)

l-Canavanine Metabolism in Jack Bean, Canavalia ensiformis (L.) DC. (Leguminosae)

Sibs with mental and physical retardation and trichorrhexis nodosa with abnormal amino acid composition of the hair.

Enzymes of Arginine and Urea Systhesis

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Product

Resources

About

Separation and Properties of Argininosuccinate and Its Two Anhydrides and Their Detection in Biological Materials^*