Total synthesis of the NodRm-IV factors, the rhizobium nodulation signals

Nicolaou, K. C.; Bockovich, N. J.; Carcanague, Daniel R.; Hummel, C. W.; Even, Lea

doi:10.1021/ja00048a054

Cited by 83 publications

(35 citation statements)

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“…First, synthetic LCOs are biologically active. Although there are now four published reports of the synthesis of various LCO molecules (Nicolaou et al, 1992;Wang et al, 1993;Ikeshita et al, 1994aIkeshita et al, , 1994b, there has only recently been a published report of HAD activity for synthetic LCOs (Bono et al, 1995). Our study demonstrates that synthetic LCO molecules not only deform root hairs but also induce emerging nodule structures.…”

Section: Discussionmentioning

confidence: 46%

Structural Requirements of Synthetic and Natural Product Lipo-Chitin Oligosaccharides for Induction of Nodule Primordia on Glycine soja

et al. 1995

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Rhizobia synthesize a class of lipo-chitin oligosaccharides that induce root hair deformation and induce the initiation of nodule structures on legume roots. These lipo-chitin oligosaccharides are tetra-and penta-lipo-oligosaccharides of N-acetylglucosamine with an acyl substitution on the nonreducing end and are commonly known as Nod factors. In this study, we demonstrate that synthetic analogs of natural product Nod factors have the same biological activities. To determine structure-activity relationships, a collection of synthetic and natural product lipo-chitin oligosaccharides was assayed on Glycine soja. All biologically active lipo-chitin oligosaccharides induced both root hair deformation and nodule initiations on C. soja. The most active lipo-chitin oligosaccharides deformed root hairs at 1O-l' M and induced nodules at 1 ng of lipo-chitin oligosaccharide per spot inoculation. Plant responses demonstrate an interdependence of backbone length and the presence of substitutions on the reducing end. Lipo-chitin oligosaccharides containing four Kacetylglucosamine residues were active only without a reducing end modification, whereas lipo-chitin oligosaccharides containing five N-acetylglucosamine residues were active only with reducing end modification. The plant thus recognizes lipo-chitin oligosaccharides without reducing end substitutions despite the importance of these modifications for host range.Signal exchange between symbiotic organisms is best understood in the Xhizobium-legume symbiosis. Species of Rhizobium, Bradyrhizobium, and Azorhizobium (collectively known as rhizobia) enter into a mutualistic association with legumes in which the bacteria provide reduced nitrogen to the plant and the plant provides carbon and energy '

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Section: Discussionmentioning

confidence: 46%

Structural Requirements of Synthetic and Natural Product Lipo-Chitin Oligosaccharides for Induction of Nodule Primordia on Glycine soja

et al. 1995

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“…The following LCOs, analogs to natural NFs, were chemically synthesized by Nicolaou et al (1992): LCO-IV(Ac,S,C16:2⌬2,9), LCO-IV(S,C16:2⌬2,9), LCO-IV(Ac,C16:2⌬2,9), and LCO-IV(C16:2⌬2, 9; see Fig. 1).…”

Section: Preparation and Purification Of Nfs And Related Lcosmentioning

confidence: 99%

“…The two major natural NFs produced by S. meliloti are ␤-1,4-linked GlcNAc tetramers, O-6-sulfated on the reducing sugar, N-acylated by 2E,9Z hexadecadienoic acid on the nonreducing sugar, and either O-6-acetylated or not on C6 of this sugar; these NFs were termed NodRm-IV(Ac,S,C16:2) and NodRm-IV(S,C16:2), respectively (Roche et al, 1991a). These two compounds were chemically synthesized by Nicolaou et al (1992) (Fig. 1).…”

Section: Morphogenic Activity Of Synthetic Nfs On Alfalfa and The Impmentioning

confidence: 99%

“…The synthesis of the two O-acetylated LCOs described in the previous section required six chemical steps after the introduction of the acyl chain (Nicolaou et al, 1992). To provide direct and easy access to a collection of LCOs with different N-acyl chains in a single operation with a single precursor, we used another synthetic route in which the last step was the introduction of the acyl chain.…”

Section: Synthesis Of Lcos Differing In Their Acyl Moietymentioning

confidence: 99%

“…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%

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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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Dichlorobis(cyclopentadienyl)hafnium-Silver(I) Salts

Suzuki

Matsumoto

2001

Encyclopedia of Reagents for Organic Synthesis

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Total synthesis of the NodRm-IV factors, the rhizobium nodulation signals

Cited by 83 publications

References 1 publication

Structural Requirements of Synthetic and Natural Product Lipo-Chitin Oligosaccharides for Induction of Nodule Primordia on Glycine soja

Structural Requirements of Synthetic and Natural Product Lipo-Chitin Oligosaccharides for Induction of Nodule Primordia on Glycine soja

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

Dichlorobis(cyclopentadienyl)hafnium-Silver(I) Salts

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