1993
DOI: 10.1021/jo00063a007
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The structures of syringolides 1 and 2, novel C-glycosidic elicitors from Pseudomonas syringae pv. tomato

Abstract: The isolation and structure determination of two bacterial signal molecules which elicit active plant defense responses are reported. The production of these molecules by Gram-negative bacteria requires the action of avirulence gene D (avrD), cloned from Pseudomonas syringae pv. tomato. The structures of syringolide 1 (la) and syringolide 2 (lb) are determined by a combination of NMR experiments, biosynthetic arguments, molecular modeling, and X-ray crystallography. A proposed biosynthetic scheme based on the … Show more

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Cited by 107 publications
(69 citation statements)
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“…Syringolide 1 was obtained from culture fluids of Esckerickia coli expressing the avrD gene and was purified by HPLC on silica gel columns (Midland et al, 1993;Yucel et al, 1994). In some preliminary experiments (not shown), we used a less pure elicitor fraction that contained syringolides 1 and 2.…”
Section: Elicitormentioning
confidence: 99%
See 1 more Smart Citation
“…Syringolide 1 was obtained from culture fluids of Esckerickia coli expressing the avrD gene and was purified by HPLC on silica gel columns (Midland et al, 1993;Yucel et al, 1994). In some preliminary experiments (not shown), we used a less pure elicitor fraction that contained syringolides 1 and 2.…”
Section: Elicitormentioning
confidence: 99%
“…It has been widely postulated that avirulence genes direct the production of cultivar-specific elicitors that are recognized by plants with the complementary resistance gene (Gabriel and Rolfe, 1990;Keen, 1990;Atkinson, 1993). Severa1 such elicitors have been identified, including the coat protein of tobacco mosaic virus (Culver and Dawson, 1989), a peptide from Cladosporium fulvum (Van den Ackerveken et al, 1992), and glycolipids, called syringolides, from Pseudomonas syringae pv tomato (Midland et al, 1993). Bacterial synthesis of the syringolides is directed by the avirulence gene avrD.…”
mentioning
confidence: 99%
“…Among the Ͼ 30 bacterial AVR gene products reported in the literature, only a few have presented clues as to what this function might be. The avrD gene cloned from Pseudomonas syringae pv glycinea is believed to play a role in producing low molecular weight glycolipid elicitors (Keen et al, 1990;Midland et al, 1993). The bacterial AVR gene, avrRxv , 1 Current address: Department of Plant Pathology, University of Arizona, Tucson, AZ.…”
mentioning
confidence: 99%
“…28 It is noteworthy that the same butenolide compound has been proposed as an intermediate for syringolide biosynthesis in Pseudomonas syringae. 29 Interaction of SCP1 with S. coelicolor chromosome and other replicons SCP1 is known to interact with the S. coelicolor chromosome to generate various SCP1-chromosome hybrid structures. A 1850-kb linear DNA was found in S. coelicolor 2106, a cysD donor, which transfers a cysD phenotype in the mating with an SCP1-free strain.…”
Section: Biosynthesis Of Methylenomycin and Autoregulators In S Coelmentioning
confidence: 99%