Structure of a zwitterionic O-polysaccharide from Photorhabdus temperata subsp. cinerea 3240

Kondakova, Anna N.; Kirsheva, Nadezhda A.; Arbatsky, Nikolay P.; Shaikhutdinova, Rima Z.; Shashkov, Alexander S.; Ivanov, Sergey A.; Anisimov, Andrey P.; Knirel, Yuriy A.

doi:10.1016/j.carres.2015.01.013

Cited by 5 publications

(7 citation statements)

References 12 publications

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“…cinerea (isolated from H. downesi in Hungary), which is unique amongst bacterial polysaccharide structures and differs significantly from those of P. temperata subsp. temperata and two other Photorhabdus species [68]. Since polysaccharides with different structure have different physical properties [69], production of disparate exopolysaccharides is a plausible mechanism by which bacterial strains might differentially affect the survival of organisms with which they associate.…”

Section: Discussionmentioning

confidence: 99%

An Entomopathogenic Nematode Extends Its Niche by Associating with Different Symbionts

et al. 2016

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Bacterial symbionts are increasingly recognised as mediators of ecologically important traits of their animal hosts, with acquisition of new traits possible by uptake of novel symbionts. The entomopathogenic nematode Heterorhabditis downesi associates with two bacterial symbionts, Photorhabdus temperata subsp. temperata and P. temperata subsp. cinerea. At one intensively studied coastal dune site, P. temperata subsp. cinerea is consistently more frequently isolated than P. temperata subsp. temperata in H. downesi recovered from under the bare sand/Ammophila arrenaria of the front dunes (where harsh conditions, including drought, prevail). This is not the case in the more permissive closed dune grassland further from the sea. No differences were detected in ITS1 (internal transcribed spacer) sequence between nematode lines carrying either of the two symbiont subspecies, nor did they differ in their ability to utilise insects from three orders. The two symbionts could be readily swapped between lines, and both were carried in equal numbers within infective juveniles. In laboratory experiments, we tested whether the symbionts differentially affected nematode survival in insect cadavers that were allowed to dry. We assessed numbers of nematode infective juveniles emerging from insects that had been infected with H. downesi carrying either symbiont subspecies and then allowed to desiccate for up to 62 days. In moist conditions, cadavers produced similar numbers of nematodes, irrespective of the symbiont subspecies present, while under desiccating conditions, P. temperata subsp. cinerea cadavers yielded more nematode progeny than P. temperata subsp. temperata cadavers. Desiccating cadavers with the same nematode isolates, carrying either one or the other symbiont subspecies, confirmed that the symbiont was responsible for differences in nematode survival. Moreover, cadavers harbouring P. temperata subsp. cinerea had a reduced rate of drying relative to cadavers harbouring P. temperata subsp. temperata. Our experiments support the hypothesis that H. downesi can extend its niche into harsher conditions by associating with P. temperata subsp. cinerea.

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Section: Discussionmentioning

confidence: 99%

An Entomopathogenic Nematode Extends Its Niche by Associating with Different Symbionts

et al. 2016

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“…cinerea 3240 isolated from the larvae of the entomopathogenic nematode Heterorhabditis downesi in Hungary. 10 Photorhabdus temperata is a genus of Gramnegative entomopathogenic bacteria belonging to the family Enterobacteriaceae. The trisaccharide repeating unit (RU) consists of two unusual components, viz., 2-acetamido-4amino-2,4,6-trideoxy-D-galactose (D-FucNAc4N, AAT) and 2aminoethyl phosphate (PEtN).…”

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confidence: 78%

“…Recently, Knirel and co-workers established the structure of a zwitterionic O -polysaccharide of Photorhabdus temperata subsp. cinerea 3240 isolated from the larvae of the entomopathogenic nematode Heterorhabditis downesi in Hungary …”

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Total Synthesis of the Phosphorylated Zwitterionic Trisaccharide Repeating Unit of Photorhabdus temperata cinerea 3240

Puri

Kulkarni

2021

Org. Lett.

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Herein, we report the total synthesis of the phosphorylated zwitterionic trisaccharide repeating unit of Photorhabdus temperata subsp. cinerea 3240. The efficient route involves regio- and stereoselective assembly of trisaccharide with rare deoxyamino sugar AAT at the nonreducing end, late stage oxidation, and installation of a phosphate linker on the trisaccharide. The total synthesis was completed via a longest linear sequence of 24 steps in 6.5% overall yield.

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“…Recently, a novel zwitterionic polysaccharide (ZPS) has been identified on the cell surface of P. temperata (Figure 1C). 2 Nematodes affiliated with this microorganism showcase enhanced survival during their emergence from a cadaver. To characterize why the production of such disparate exopolysaccharides differentially affects the survival of host organisms, we initiated a campaign to synthesize the zwitterionic repeating unit.…”

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confidence: 99%

“…Recently, a novel zwitterionic polysaccharide (ZPS) has been identified on the cell surface of P. temperata (Figure C) . Nematodes affiliated with this microorganism showcase enhanced survival during their emergence from a cadaver.…”

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Total Synthesis of the Photorhabdus temperata ssp. Cinereal 3240 Zwitterionic Trisaccharide Repeating Unit

Nguyen

Townsend

2021

Org. Lett.

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Zwitterionic carbohydrate modifications, such as phosphoethanolamine (PEtN), govern host−pathogen interactions. Whereas it is recognized that these modifications stimulate the host immune system, the purpose of PEtN modification remains largely descriptive. As an enabling step toward studying this carbohydrate modification, we report a synthesis of the P. temperata zwitterionic trisaccharide repeating unit. The 32-step synthesis was enabled by H-phosphonate chemistry to install the PEtN arm on a poorly reactive and sterically hindered C4alcohol.Letter pubs.acs.org/OrgLett

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Structure of a zwitterionic O-polysaccharide from Photorhabdus temperata subsp. cinerea 3240

Cited by 5 publications

References 12 publications

An Entomopathogenic Nematode Extends Its Niche by Associating with Different Symbionts

An Entomopathogenic Nematode Extends Its Niche by Associating with Different Symbionts

Total Synthesis of the Phosphorylated Zwitterionic Trisaccharide Repeating Unit of Photorhabdus temperata cinerea 3240

Total Synthesis of the Photorhabdus temperata ssp. Cinereal 3240 Zwitterionic Trisaccharide Repeating Unit

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