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Octopinic Acid Sale

(Synonyms: (+)-Octopinic Acid) 目录号 : GC48927

An opine

Octopinic Acid Chemical Structure

Cas No.:20197-09-5

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产品描述

Octopinic acid is an opine that has been found in crown gall tumors induced by the plant pathogenic bacterium A. tumefaciens.1,2

1.Scott, I.M.Opine content of unorganised and teratomatous tobacco crown gall tissuesPlant Sci. Lett.16(2-3)239-248(1979) 2.Menage, A., and Morel, G.Presence of a new amino acid in crowngall tissueC. R. Acad. Sci.261(9)2001-2002(1965)

Chemical Properties

Cas No. 20197-09-5 SDF
别名 (+)-Octopinic Acid
Canonical SMILES O=C(C(C)NC(CCCN)C(O)=O)O
分子式 C8H16N2O4 分子量 204.2
溶解度 储存条件 -20°C
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1 mM 4.8972 mL 24.4858 mL 48.9716 mL
5 mM 0.9794 mL 4.8972 mL 9.7943 mL
10 mM 0.4897 mL 2.4486 mL 4.8972 mL
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Research Update

Isolation and characterization of Agrobacterium tumefaciens mutants affected in the utilization of octopine, Octopinic Acid and lysopine

J Gen Microbiol 1976 Sep;96(1):155-63.PMID:978177DOI:10.1099/00221287-96-1-155.

Using an enrichment procedure, mutant strains of Agrobacterium tumefaciens were isolated that lacked the ability to utilize octopine as a nitrogen source. Of 55 such isolates, 44 were unable to utilize several amino acids; the remaining 11 strains were altered solely in their ability to utilize octopine, Octopinic Acid and lysopine. It is concluded that only the latter were plasmid mutations. Among them, there was a high, but no absolute, correlation with avirulence. All strains contained the T1 plasmid. All virulent strains showed active transport of octopine when they had previously been grown in medium containing octopine, whereas the avirulent strains failed to show such transport. All the virulent mutants induced tumours containing octopine. The results are discussed in relation to the hypothesis that the genes which code for the octopine synthesizing enzymes in the tumour are of bacterial origin.

Specificity of octopine uptake by Rhizobium and pseudomonas strains

Appl Environ Microbiol 1990 May;56(5):1453-8.PMID:16348194DOI:10.1128/aem.56.5.1453-1458.1990.

The octopine-utilizing strain Agrobacterium tumefaciens B6S3 and three nonagrobacteria which had the capacity to utilize this opine were compared for octopine uptake. The characteristics of uptake by Rhizobium meliloti A3 and strain B6S3 were similar. In both bacteria, uptake activity was inducible by octopine and by the related opine Octopinic Acid, and competition assays showed that these two opine substrates were accepted by the same uptake system with an equivalent affinity. Cells of Pseudomonas putida 203 accumulated octopine against a concentration gradient, and this activity was induced specifically by octopine. While strain 203 did not utilize Octopinic Acid, a spontaneous mutant with a combined capacity for octopine and Octopinic Acid utilization was obtained. Both opines induced octopine uptake by this mutant, but Octopinic Acid was not a substrate for the induced system. Thus, the Pseudomonas uptake system exhibited a different specificity for octopine than the corresponding Agrobacterium system. The nonfluorescent pseudomonad GU187j, which utilized the three related opines octopine, Octopinic Acid, and nopaline, was constitutive for octopine uptake. Strain GU187j possessed a system which accepted these three opines, but not arginine or ornithine, with a similar affinity.

Fungal catabolism of crown gall opines

Appl Environ Microbiol 1990 Jan;56(1):150-5.PMID:16348087DOI:10.1128/aem.56.1.150-155.1990.

This study was conducted to determine the capacities of 37 fungi to utilize various crown gall opines as their sole carbon and nitrogen source. One strain of Fusarium solani, two of Cylindrocarpon destructans, and six of Cylindrocarpon heteronema catabolized octopine, mannopine, Octopinic Acid, succinamopine, or a combination of these opines. One C. heteronema and one Fusarium dimerum strain grew only on succinamopine. None of the fungal isolates had the ability to grow on nopaline. The catabolism of opines by fungi was confirmed by the disappearance of the opine from the growth medium and by an increase in final mycelial dry weight with rising initial concentration of test substrate. This study thus shows that the catabolism of opines is not restricted to bacteria.

In Vivo Synthesis of Crown Gall-specific Agrobacterium tumefaciens-directed Derivatives of Basic Amino Acids

Plant Physiol 1978 Jul;62(1):26-30.PMID:16660462DOI:10.1104/pp.62.1.26.

Several kinds of primary sunflower (Helianthus annuus) crown gall tissues were established in tissue culture and then labeled in vivo with either [(14)C]arginine, [(14)C]histidine, [(3)H]lysine, or [(3)H]ornithine. Crown gall tissues incited by Agrobacterium tumefaciens strains that utilize octopine as a sole source of carbon or nitrogen for growth synthesized the four members of the N(2)-(1-carboxyethyl)-amino acid family: octopine, histopine, lysopine, and Octopinic Acid. Those tissues incited by A. tumefaciens strains that utilize nopaline synthesized nopaline and two new compounds, a lysine and an ornithine derivative (ornaline). A normal tissue culture, a habituated tissue culture, and a crown gall culture from a strain of the bacteria unable to utilize either octopine or nopaline did not synthesize any of the amino acid derivatives. We could not detect any other crown gall-specific derivatives of the four basic amino acids.

Growth of Octopine-Catabolizing Pseudomonas spp. under Octopine Limitation in Chemostats and Their Potential To Compete with Agrobacterium tumefaciens

Appl Environ Microbiol 1990 Sep;56(9):2834-9.PMID:16348292DOI:10.1128/aem.56.9.2834-2839.1990.

The growth characteristics of five octopine-catabolizing pseudomonads have been determined in batch and continuous cultures. All five strains belonged to rRNA homology group I and showed a more psychrotrophic growth pattern than did Agrobacterium tumefaciens B6 and ATCC 15955. In chemostats limited by octopine, either as the source of carbon and nitrogen or the sole source of nitrogen, maximum specific growth rates and substrate affinities were lower than those in chemostats limited by glutamate. These growth dynamics were similar to those observed for Agrobacterium strains B6 and ATCC 15955 even though the catabolic genes and pathways are believed to be different in the two genera. An analysis of the yields in octopine-limited chemostats indicated that the use of octopine as the sole source of carbon and nitrogen was grossly inefficient. Octopine and presumably lysopine and Octopinic Acid provided a better source of nitrogen than of carbon. One of the Pseudomonas fluorescens strains, E175D, was able to produce its highest yield on octopine as a nitrogen source. Competition models formulated on pure culture parameters indicated that two of the Pseudomonas spp. would dominate A. tumefaciens B6 and ATCC 15955 when in simple competition for octopine as a limiting substrate.