Synthesis and structural modeling of the amphiphilic siderophore rhizobactin-1021 and its analogs

Fadeev, Evgeny A.; Luo, Minkui; Groves, John T.

doi:10.1016/j.bmcl.2005.05.114

Cited by 8 publications

(5 citation statements)

References 22 publications

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“…In our synthetic strategy for 1ab-4ab, cyclic anhydride 8 was used as a common intermediate. 6) Compound 8 was synthesized as follows (Chart 2): 1) Selective esterification of the outer two carboxy groups in CA to provide bis-methyl ester 5. 7) 2) Esterification on the remaining carboxy group to form tert-butyl ester 6.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Biosynthetic Intermediates of Vibrioferrin and Enzyme Reactions Using Them as Substrates

Mitome,

Tanabe,

Funahashi

et al. 2024

CHEMICAL & PHARMACEUTICAL BULLETIN

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Section: Resultsmentioning

confidence: 99%

Synthesis of Biosynthetic Intermediates of Vibrioferrin and Enzyme Reactions Using Them as Substrates

Mitome,

Tanabe,

Funahashi

et al. 2024

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The lipophilic tail is thought to affect membrane affinity and prevent diffusion in sea water. 50 , 51 Yet, little is known about the strategic advantage of such fatty acid appendages in soil. One explanation could be that Chryseobacterium spp.…”

Section: Resultsmentioning

confidence: 99%

Chryseochelins—structural characterization of novel citrate-based siderophores produced by plant protecting Chryseobacterium spp.

Rehm

Vollenweider

et al. 2023

Metallomics

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Bacteria secrete siderophores whose function is to acquire iron. In recent years, the siderophores of several Chryseobacterium species were shown to promote the health and growth of various plants such as tomato or rice. However, the chemical nature of Chryseobacterium siderophores remained unexplored despite great interest. In this work, we present the purification and structure elucidation by NMR and MS/MS of chryseochelin A, a novel citrate-based siderophore secreted by three Chryseobacterium strains involved in plant protection. It contains the unusual building blocks 3-hydroxycadaverine and fumaric acid. Furthermore, the unstable structural isomer chryseochelin B and its stable derivative containing fatty acid chains, named chryseochelin C, were identified by mass spectrometric methods. The latter two incorporate an unusual ester connectivity to the citrate moiety showing similarities to achromobactin from the plant pathogen Dickeya dadantii. Finally, we show that chryseochelin A acts in a concentration-dependent manner against the plant-pathogenic Ralstonia solanacearum strain by reducing its access to iron. Thus, our study provides valuable knowledge about the siderophores of Chryseobacterium strains, which have great potential in various applications.

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“…These spacers, in turn, are acylated and derivatized by a N-hydroxy group thus forming hydroxamic acids. For a synthesis concept see (404).…”

Section: Siderophores With Two Hydroxamic Acid Unitsmentioning

confidence: 99%

“…Its Fe 3+ complex in aqueous solution is L-configured and forms an equilibrium between a monomeric and a dimeric form that can be separated by chromatography. A synthesis is described (404).…”

Section: Siderophores With Two Hydroxamic Acid Unitsmentioning

confidence: 99%

Microbial Siderophores

Budzikiewicz

2010

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, Vol. 92

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Synthesis and structural modeling of the amphiphilic siderophore rhizobactin-1021 and its analogs

Cited by 8 publications

References 22 publications

Synthesis of Biosynthetic Intermediates of Vibrioferrin and Enzyme Reactions Using Them as Substrates

Synthesis of Biosynthetic Intermediates of Vibrioferrin and Enzyme Reactions Using Them as Substrates

Chryseochelins—structural characterization of novel citrate-based siderophores produced by plant protecting Chryseobacterium spp.

Microbial Siderophores

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