Synthesis of the root nodule-inducing factor NodRm-IV(C16:2,S) of rhizobium meliloti and related compounds

Ikeshita, Shinji; Sakamoto, Akio; Nakahara, Yuko; Nakahara, Yoshiaki; Ogawa, Tomoya

doi:10.1016/s0040-4039(00)76846-8

Cited by 36 publications

(9 citation statements)

References 18 publications

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“…The chemical synthesis of NFs of S. meliloti (Nicolaou et al, 1992;Wang et al, 1993;Ikeshita et al, 1994;Tailler et al, 1994) and B. japonicum (Ikeshita et al, 1995) has now been achieved, making possible the synthesis of a variety of chemically pure authentic NFs, the introduction of single, defined, structural modifications, and the synthesis of analogs that may not occur naturally. Stokkermans et al (1995) used synthetic NFs and related LCOs to study NF structural requirements to elicit symbiotic responses in soybean, a plant nodulated by rhizobia that produce fucosylated NFs and do not possess active nodFE genes.…”

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confidence: 99%

Nodule-Inducing Activity of Synthetic Sinorhizobium meliloti Nodulation Factors and Related Lipo-Chitooligosaccharides on Alfalfa.Importance of the Acyl Chain Structure1

et al. 1999

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Sinorhizobium meliloti nodulation factors (NFs) elicit a number of symbiotic responses in alfalfa (؊7 M. The optimal chain length was C16, with the C16-LCO being more than 10-fold more active than the C12-and C18-LCOs. Unsaturations were important, and the diunsaturated 2E,9Z LCO was more active than the monounsaturated LCOs. We discuss different hypotheses for the role of the acyl chain in NF perception.

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confidence: 99%

Nodule-Inducing Activity of Synthetic Sinorhizobium meliloti Nodulation Factors and Related Lipo-Chitooligosaccharides on Alfalfa.Importance of the Acyl Chain Structure1

et al. 1999

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“…The final step of the synthesis involves a selective coupling reaction between the free amine and fatty acids. This coupling was done by selective acylation with the N ‐hydroxysuccinimide ester37c,e, 40 of oleic acid (C18:1Δ9Z; 28 )41 or of palmitic acid (C16:0; 29 )42 in DMSO at 60 °C in the presence of an excess of triethylamine (Scheme ). This reaction afforded the targeted Nod factors 30 and 31 and the Myc factors 32 and 33 in yields ranging from 78 % to quantitative and in good purities.…”

Section: Methodsmentioning

confidence: 99%

From Chitin to Bioactive Chitooligosaccharides and Conjugates: Access to Lipochitooligosaccharides and the TMG‐chitotriomycin

Despras¹,

Alix²,

Urban³

et al. 2014

Angewandte Chemie

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The direct and chemoselective N‐transacylation of peracetylated chitooligosaccharides (COSs), readily obtained from chitin, to give per‐N‐trifluoroacetyl derivatives offers an attractive route to size‐defined COSs and derived glycoconjugates. It involves the use of various acceptor building blocks and trifluoromethyl oxazoline dimer donors prepared with efficiency and highly reactive in 1,2‐trans glycosylation reactions. This method was applied to the preparation of the important symbiotic glycolipids which are highly active on plants and to the TMG‐chitotriomycin, a potent and specific inhibitor of insect, fungal, and bacterial N‐acetylglucosaminidases.

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“…The synthetic route also enabled the incorporation of four tritium atoms in the C16:2 fatty acid chain, providing a ligand identical to the genuine NodSm factor, with a specific radioactivity high enough to perform radioligand binding experiments [11]. Other groups further proposed alternative strategies for the synthesis of the NodSm factor [12][13][14] or the Nod factors produced by Bradyrhizobium japonicum, the symbiont of soybean [15]. The procedure established by Tailler et al [13] enabled the synthesis of a series of tetrameric sulfated LCOs differing for the structure of the fatty acid (length, degree and position of unsaturations) to perform structure-function studies [16].…”

Section: Chemical Synthesis Of Nod Factorsmentioning

confidence: 99%

Lipo-chitooligosaccharidic nodulation factors and their perception by plant receptors

Fliegmann

Bono

2015

Glycoconj J

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Lipo-chitooligosaccharides produced by nitrogen-fixing rhizobia are signaling molecules involved in the establishment of an important agronomical and ecological symbiosis with plants. These compounds, known as Nod factors, are biologically active on plant roots at very low concentrations indicating that they are perceived by specific receptors. This article summarizes the main strategies developed for the syntheses of bioactive Nod factors and their derivatives in order to better understand their mode of perception. Different Nod factor receptors and LCO-binding proteins identified by genetic or biochemical approaches are also presented, indicating perception mechanisms that seem to be more complicated than expected, probably involving multi-component receptor complexes.

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Synthesis of the root nodule-inducing factor NodRm-IV(C16:2,S) of rhizobium meliloti and related compounds

Cited by 36 publications

References 18 publications

Nodule-Inducing Activity of Synthetic Sinorhizobium meliloti Nodulation Factors and Related Lipo-Chitooligosaccharides on Alfalfa.Importance of the Acyl Chain Structure1

Nodule-Inducing Activity of Synthetic Sinorhizobium meliloti Nodulation Factors and Related Lipo-Chitooligosaccharides on Alfalfa.Importance of the Acyl Chain Structure1

From Chitin to Bioactive Chitooligosaccharides and Conjugates: Access to Lipochitooligosaccharides and the TMG‐chitotriomycin

Lipo-chitooligosaccharidic nodulation factors and their perception by plant receptors

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