Synthesis and characterization of tyramine-derivatized (1 å 4)-linked α-d-oligogalacturonides

Spiro, Mark D.; Ridley, Brent L.; Glushka, John; Darvill, Alan G.; Albersheim, Peter

doi:10.1016/0008-6215(96)00075-4

Cited by 9 publications

(2 citation statements)

References 17 publications

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“…Oligogalacturonides derivatized with tyramine or biotinx-hydrazide (6-[biotinoylamino] caproic acid hydrazide) at C-1 of the reducing-end galacturonic acid were synthesized and purified to homogeneity as described previously (Spiro et al, 1996;Ridley et al, 1997).…”

Section: Preparation Of Homogeneous Oligogalacturonides and Their Redmentioning

confidence: 99%

Biological Activity of Reducing-End-Derivatized Oligogalacturonides in Tobacco Tissue Cultures1

et al. 1998

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The biological activity of reducing-end-modified oligogalacturonides was quantified in four tobacco (Nicotiana tabacum) tissue culture bioassays. The derivatives used were oligogalacturonides with the C-1 of their reducing end (a) covalently linked to a biotin hydrazide, (b) covalently linked to tyramine, (c) chemically reduced to a primary alcohol, or (d) enzymatically oxidized to a carboxylic acid. These derivatives were tested for their ability to (a) alter morphogenesis of N. tabacum cv Samsun thin cell-layer explants, (b) elicit extracellular alkalinization by suspension-cultured cv Samsun cells, (c) elicit extracellular alkalinization by suspensioncultured N. tabacum cv Xanthi cells, and (d) elicit H 2 O 2 accumulation in the cv Xanthi cells. In all four bioassays, each of the derivatives had reduced biological activity compared with the corresponding underivatized oligogalacturonides, demonstrating that the reducing end is a key element for the recognition of oligogalacturonides in these systems. However, the degree of reduction in biological activity depends on the tissue culture system used and on the nature of the specific reducing-end modification. These results suggest that oligogalacturonides are perceived differently in each tissue culture system.Carbohydrates that act as signal molecules in plants (oligosaccharins) have been isolated from plant and fungal cell wall polysaccharides, from the cell walls of bacterial symbionts of plants, and from fungal glycopeptides (for review, see Ryan and Farmer, 1991;Darvill et al., 1992;Cô té and Hahn, 1994). We are interested in determining the mechanism by which one type of the plant cell wallderived oligosaccharins, the oligogalacturonides, elicit biological responses in plants.The biological effects elicited in plants by oligosaccharins are diverse (for review, see Ryan and Farmer, 1991;Darvill et al., 1992;Cô té and Hahn, 1994) but can generally be placed in two groups: delayed responses and rapid responses. Delayed responses are usually observed hours or days after oligosaccharin treatment and are often directly involved in adaptation to environmental conditions, whereas rapid responses generally occur at the plant cell surface and are observed within minutes after addition of oligosaccharins. The delayed responses elicited by oligogalacturonides can be broadly divided into those in which defense responses are induced and those in which growth and development are modified. The defense-related responses, depending on the plant species, include phytoalexin accumulation (Hahn et al., 1981), lignification of cell walls (Robertsen, 1986), and proteinase inhibitor accumulation (Bishop et al., 1984). The responses involving growth and development include induction of ethylene in tomato fruit (Brecht and Huber, 1988), inhibition of auxin-induced pea stem elongation (Branca et al., 1988), and regulation of tobacco (Nicotiana tabacum) TCL explant morphogenesis (Eberhard et al., 1989). The rapid responses induced by oligogalacturonides include enhanced protein phosp...

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Section: Preparation Of Homogeneous Oligogalacturonides and Their Redmentioning

confidence: 99%

Biological Activity of Reducing-End-Derivatized Oligogalacturonides in Tobacco Tissue Cultures1

et al. 1998

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“…The multiple forms observed at pH 5 could possibly be the result of lactonization involving the reducing ends. 22 For G3-PDHA, reduction was also investigated at 40 °C in order to possibly increase the reaction rate.…”

Section: Reduction Of Oximes/hydrazones/n-pyranosides With α-Picoline...mentioning

confidence: 99%

Alginate-based diblock polymers: preparation, characterization and Ca-induced self-assembly

Solberg

Aachmann

et al. 2021

Polym. Chem.

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A Method for Biotin Labeling of Biologically Active Oligogalacturonides Using a Chemically Stable Hydrazide Linkage

Ridley

Spiro

Glushka

et al. 1997

Analytical Biochemistry

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Synthesis and characterization of tyramine-derivatized (1 å 4)-linked α-d-oligogalacturonides

Cited by 9 publications

References 17 publications

Biological Activity of Reducing-End-Derivatized Oligogalacturonides in Tobacco Tissue Cultures1

Biological Activity of Reducing-End-Derivatized Oligogalacturonides in Tobacco Tissue Cultures1

Alginate-based diblock polymers: preparation, characterization and Ca-induced self-assembly

A Method for Biotin Labeling of Biologically Active Oligogalacturonides Using a Chemically Stable Hydrazide Linkage

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