Rhizobium leguminosarum bv. trifolii produces Lipo-chitin Oligosaccharides with nodE-dependent Highly Unsaturated Fatty Acyl Moieties

Drift, Koen M. G. M. van der; Spaink, Herman P.; Bloemberg, Guido V.; Brussel, A. A. N. Van; Lugtenberg, Ben; Haverkamp, Johan; Thomas‐Oates, Jane

doi:10.1074/jbc.271.37.22563

Cited by 28 publications

(17 citation statements)

References 19 publications

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“…For this purpose the following compounds can act as the matrix: thioglycerol [246,247], m-nitrobenzyl alcohol [247], glycerol [248–250], dithiothreitol [251], 2,4-dinitrobenzyl alcohol, or dithiothreitol-thioglycerol (1:1, v/v) [223]. The mass spectrometer usually operates in positive-ion mode, most often producing [M+H] + ions [246,248,249,252] but also [M+Na] + [250,251] or [M+K] + [251].…”

Section: Application Of Spectroscopic Methods For Analyzing the Stmentioning

confidence: 99%

“…The mass spectrometer usually operates in positive-ion mode, most often producing [M+H] + ions [246,248,249,252] but also [M+Na] + [250,251] or [M+K] + [251]. The atom gun is operated at 6–8 kV with xenon as the bombarding gas [246,247,250,251]. This type of ion source cooperates with collision-induced dissociation tandem mass spectrometry (FAB-CID) measurements [246,247,252].…”

Section: Application Of Spectroscopic Methods For Analyzing the Stmentioning

confidence: 99%

“…The atom gun is operated at 6–8 kV with xenon as the bombarding gas [246,247,250,251]. This type of ion source cooperates with collision-induced dissociation tandem mass spectrometry (FAB-CID) measurements [246,247,252]. To obtain FAB-CID-MS/MS spectra, the collision is caused by helium, and a 10 kV accelerating voltage is used [246,247].…”

Section: Application Of Spectroscopic Methods For Analyzing the Stmentioning

confidence: 99%

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Application of Spectroscopic Methods for Structural Analysis of Chitin and Chitosan

et al. 2010

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Chitin, the second most important natural polymer in the world, and its N-deacetylated derivative chitosan, have been identified as versatile biopolymers for a broad range of applications in medicine, agriculture and the food industry. Two of the main reasons for this are firstly the unique chemical, physicochemical and biological properties of chitin and chitosan, and secondly the unlimited supply of raw materials for their production. These polymers exhibit widely differing physicochemical properties depending on the chitin source and the conditions of chitosan production. The presence of reactive functional groups as well as the polysaccharide nature of these biopolymers enables them to undergo diverse chemical modifications. A complete chemical and physicochemical characterization of chitin, chitosan and their derivatives is not possible without using spectroscopic techniques. This review focuses on the application of spectroscopic methods for the structural analysis of these compounds.

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Section: Application Of Spectroscopic Methods For Analyzing the Stmentioning

confidence: 99%

Section: Application Of Spectroscopic Methods For Analyzing the Stmentioning

confidence: 99%

Section: Application Of Spectroscopic Methods For Analyzing the Stmentioning

confidence: 99%

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Application of Spectroscopic Methods for Structural Analysis of Chitin and Chitosan

et al. 2010

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“…Modi®cations of this basic structure are very important for host speci®city in the nodulation process. In the case of Rhizobium leguminosarum and R. meliloti these modi®cations include the presence of an unusual N-linked fatty acid that has trans double bonds conjugated to the carbonyl group (Lerouge et al 1990;Spaink et al 1991;Spaink et al 1995;van der Drift et al 1996).…”

Section: Introductionmentioning

confidence: 99%

Functional analysis of an interspecies chimera of acyl carrier proteins indicates a specialized domain for protein recognition

et al. 1998

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The nodulation protein NodF of Rhizobium shows 25% identity to acyl carrier protein (ACP) from Escherichia coli (encoded by the gene acpP). However, NodF cannot be functionally replaced by AcpP. We have investigated whether NodF is a substrate for various E. coli enzymes which are involved in the synthesis of fatty acids. NodF is a substrate for the addition of the 4'-phosphopantetheine prosthetic group by holo-ACP synthase. The Km value for NodF is 61 microM, as compared to 2 microM for AcpP. The resulting holo-NodF serves as a substrate for coupling of malonate by malonyl-CoA:ACP transacylase (MCAT) and for coupling of palmitic acid by acyl-ACP synthetase. NodF is not a substrate for beta-keto-acyl ACP synthase III (KASIII), which catalyses the initial condensation reaction in fatty acid biosynthesis. A chimeric gene was constructed comprising part of the E. coli acpP gene and part of the nodF gene. Circular dichroism studies of the chimeric AcpP-NodF (residues 1-33 of AcpP fused to amino acids 43-93 of NodF) protein encoded by this gene indicate a similar folding pattern to that of the parental proteins. Enzymatic analysis shows that AcpP-NodF is a substrate for the enzymes holo-ACP synthase, MCAT and acyl-ACP synthetase. Biological complementation studies show that the chimeric AcpP-NodF gene is able functionally to replace NodF in the root nodulation process in Vicia sativa. We therefore conclude that NodF is a specialized acyl carrier protein whose specific features are encoded in the C-terminal region of the protein. The ability to exchange domains between such distantly related proteins without affecting conformation opens exciting possibilities for further mapping of the functional domains of acyl carrier proteins (i. e., their recognition sites for many enzymes).

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“…The nodHPQ genes, which are also found in S. meliloti and Rhizobium tropici, have been shown to specify O sulfation of the Nod factor reducing end in these two species (11,18,29). The nodFE genes, which are also present in S. meliloti and R. leguminosarum, determine in these two species the synthesis of various polyunsaturated fatty acids with one or several double bounds conjugated to the carbonyl group (7,34,39). Therefore, one might expect the Mesorhizobium sp.…”

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Unusual Methyl-Branched α,β-Unsaturated Acyl Chain Substitutions in the Nod Factors of an Arctic Rhizobium, Mesorhizobium sp. Strain N33 ( Oxytropis arctobia )

et al. 2001

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Mesorhizobium sp. strain N33 (Oxytropis arctobia), a rhizobial strain isolated in arctic Canada, is able to fix nitrogen at very low temperatures in association with a few arctic legume species belonging to the genera Astragalus, Onobrychis, and Oxytropis. Using mass spectrometry and nuclear magnetic resonance spectroscopy, we have determined the structure of N33 Nod factors, which are major determinants of nodulation. They are pentameric lipochito-oligosaccharides 6-O sulfated at the reducing end and exhibit other original substitutions: 6-O acetylation of the glucosamine residue next to the nonreducing terminal glucosamine and N acylation of the nonreducing terminal glucosamine by methyl-branched acyl chains of the iso series, some of which are ␣,␤ unsaturated. These unusual substitutions may contribute to the peculiar host range of N33. Analysis of N33 whole-cell fatty acids indicated that synthesis of the methyl-branched fatty acids depended on the induction of bacteria by plant flavonoids, suggesting a specific role for these fatty acids in the signaling process between the plant and the bacteria. Synthesis of the methyl-branched ␣,␤-unsaturated fatty acids required a functional nodE gene.Rhizobia are soil bacteria, now classified in several genera (e.g., Rhizobium, Sinorhizobium, Mesorhizobium, Bradyrhizobium, Azorhizobium), which form a symbiotic association with legume plants. The interaction between bacteria and plants results in the formation of nodules on the host plant roots, in which rhizobia fix atmospheric nitrogen. The association between rhizobia and legumes is specific: each rhizobial strain has a defined host range. For example, Mesorhizobium sp. strain N33, isolated from Oxytropis arctobia, also nodulates Astragalus alpinus and Onobrychis viciifolia (19,26). In contrast, Sinorhizobium meliloti efficiently nodulates alfalfa (Medicago sativa) as well as Melilotus and Trigonella species. Mesorhizobium sp. strain N33 was isolated in the Canadian high arctic and is able to grow and fix nitrogen at temperatures as low as 5°C. In addition, it was shown that arctic rhizobia promoted better growth of O. viciifolia at low temperatures than did temperate strains (27). Thus, it might be valuable to extend the host range of arctic rhizobia to agronomically important legumes, in order to improve nitrogen fixation by these plants at low temperatures. It is therefore important to understand the molecular mechanisms controlling the nodulation specificity of arctic rhizobia.Earlier work has shown that nodulation and host specificity in rhizobium-legume symbiosis are determined by signal exchanges between the bacteria and the host plant (21). Flavonoids excreted by the plant roots induce the expression of rhizobial nodulation (nod) genes. Most of these genes are involved in the biosynthesis and secretion of bacterial signals, the Nod factors, that can specifically induce symbiotic responses of the host plants. These responses include root hair deformation, division of root cortical cells and, in some instances,...

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Rhizobium leguminosarum bv. trifolii produces Lipo-chitin Oligosaccharides with nodE-dependent Highly Unsaturated Fatty Acyl Moieties

Cited by 28 publications

References 19 publications

Application of Spectroscopic Methods for Structural Analysis of Chitin and Chitosan

Application of Spectroscopic Methods for Structural Analysis of Chitin and Chitosan

Functional analysis of an interspecies chimera of acyl carrier proteins indicates a specialized domain for protein recognition

Unusual Methyl-Branched α,β-Unsaturated Acyl Chain Substitutions in the Nod Factors of an Arctic Rhizobium, Mesorhizobium sp. Strain N33 ( Oxytropis arctobia )

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