Complexation of cyclic dodecadepsipeptide, Cereulide with ammonium salts

Pitchayawasin, Suthasinee; Kuse, Masaki; Koga, Kazushi; Isobe, Mitsuaki; Agata, Norio; Ohta, Michio

doi:10.1016/s0960-894x(03)00731-5

Cited by 20 publications

(18 citation statements)

References 7 publications

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“…Fig. 3 summarizes the effect of a subset of alkali metal salts examined, with attention to those reported to bind peptides and depsipeptides in solution (45)(46)(47)(48)(49)(50). Weakly coordinating counteranions were chosen for their respective alkali metal cation to promote solubility of the salt additive and interaction of the metal cation with the growing depsipeptide chain.…”

Section: Significancementioning

confidence: 99%

Rapid synthesis of cyclic oligomeric depsipeptides with positional, stereochemical, and macrocycle size distribution control

Batiste

Johnston

2016

Proc. Natl. Acad. Sci. U.S.A.

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Macrocyclic small molecules are attractive tools in the development of sensors, new materials, and therapeutics. Within early-stage drug discovery, they are increasingly sought for their potential to interact with broad surfaces of peptidic receptors rather than within their narrow folds and pockets. Cyclization of linear small molecule precursors is a straightforward strategy to constrain conformationally mobile motifs, but forging a macrocycle bond typically becomes more difficult at larger ring sizes. We report the development of a general approach to discrete collections of oligomeric macrocyclic depsipeptides using an oligomerization/macrocyclization process governed by a series of Mitsunobu reactions of hydroxy acid monomers. Ring sizes of 18, 24, 30, and 36 are formed in a single reaction from a didepsipeptide, whereas sizes of 24, 36, and 60 result from a tetradepsipeptide. The ring-size selectivity inherent to the approach can be modulated by salt additives that enhance the formation of specific ring sizes. Use of chemical synthesis to prepare the monomers suggests broad access to functionally and stereochemically diverse collections of natural product-like oligodepsipeptide macrocycles. Two cyclodepsipeptide natural products were prepared along with numerous unnatural oligomeric congeners to provide rapid access to discrete collections of complex macrocyclic small molecules from medium (18) to large (60) ring sizes.Mitsunobu | total synthesis | collective | macrocycle | oligomerization I nterest in the preparation and use of small molecules exhibiting macrocyclic rings is growing at a tremendous pace, driving the development of new approaches, new chemical reactions, and the underlying chemistry and tools (catalysts) to support them. Historically, studies of macrocyclization reactions have been guided by natural products bearing unusually large carbocycles or mediumand large-ring lactones, amides, and ethers. Fragmentation reactions of polycyclic molecules have long played a role in access to medium-sized macrocycles, whereas macrocyclizations to lactones and amides are often accomplished from linear precursors at high dilution. Insofar as these efforts were typically driven by the goal to prepare a specific macrocycle, often in the form relevant to a natural product synthesis or an engineered constraint to a peptide, absent from the field is an approach that provides rapid access to collections (1) of natural product-like macrocycles, particularly from stereochemically complex, functionally rich, linear precursors (2-6).Pioneers in this area have recorded some success (Fig. 1). Esterification reactions of activated hydroxy acids have led predominantly to diolides, (7-10) and in a single case, oligolides (11). Amidation reactions of activated polypeptides were central to the preparations of macrocyclic peptides by Rothe and Kreiss (12,13) and Wipf and coworkers (14, 15), but they were low yielding and size nonselective. Burke and coworkers (16,17) have shown that the efficiency of an 18-membered oligol...

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Section: Significancementioning

confidence: 99%

Rapid synthesis of cyclic oligomeric depsipeptides with positional, stereochemical, and macrocycle size distribution control

Batiste

Johnston

2016

Proc. Natl. Acad. Sci. U.S.A.

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“…Cereulide is a K ϩ ionophore and it has toxin activity when the K ϩ ion is held in the molecule (18). The proportion of K ϩ form in the preparation of cereulide varies according to the extraction method (21). Therefore, values by a bioassay and those by a mass spectrometry sometimes dissociate from each other.…”

Section: Discussionmentioning

confidence: 99%

Quantitative Analysis of Cereulide, an Emetic Toxin of Bacillus cereus, by Using Rat Liver Mitochondria

Kawamura-Sato

Hirama

Agata³

et al. 2005

Microbiology and Immunology

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An emetic toxin cereulide, produced by Bacillus cereus, causes emetic food poisonings, but a method for quantitative measurement of cereulide has not been well established. A current detection method is a bioassay method using the HEp‐2 cell vacuolation test, but it was unable to measure an accurate concentration. We established a quantitative assay for cereulide based on its mitochondrial respiratory uncoupling activity. The oxygen consumption in a reaction medium containing rat liver mitochondria was rapid in the presence of cereulide. Thus uncoupling effect of cereulide on mitochondrial respiration was similar to those of uncouplers 2,4‐dinitrophenol (DNP), carbonylcyanide m‐chlorophenylhydrazone (CCCP), and valinomycin. This method gave constant results over a wide range of cereulide concentrations, ranging from 0.05 to 100 μg/ml. The minimum cereulide concentration to detect uncoupled oxygen consumption was 50 ng/ml and increased dose‐dependently to the maximum level. Semi‐log relationship between the oxygen consumption rate and the cereulide concentraiton enables this method to quantify cereulide. The results of this method were highly reproducible as compared with the HEp‐2 cell vacuolation test and were in good agreement with those of the HEp‐2 cell vacuolation test. The enterotoxin of B. cereus or Staphylococcus aureus did not show any effect on the oxygen consumption, indicating this method is specific for the identification of cereulide as a causative agent of emetic food poisonings.

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“…Evaluation of the cation complexation by 1 H or 13 C NMR methods, in solution or solid-state, has been reported for thel ionophores: valinomycin [703–706], nonactin and tetranactin [707], and cereulide [708]. Potassium ions cause significant interference in ammonium ion detection because the potassium ion is similar in size to the ammonium ion (1.33 Å) [118].…”

Section: Reviewmentioning

confidence: 99%

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Späth¹,

König²

2010

Beilstein J. Org. Chem.

220

130

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SummaryAmmonium ions are ubiquitous in chemistry and molecular biology. Considerable efforts have been undertaken to develop synthetic receptors for their selective molecular recognition. The type of host compounds for organic ammonium ion binding span a wide range from crown ethers to calixarenes to metal complexes. Typical intermolecular interactions are hydrogen bonds, electrostatic and cation–π interactions, hydrophobic interactions or reversible covalent bond formation. In this review we discuss the different classes of synthetic receptors for organic ammonium ion recognition and illustrate the scope and limitations of each class with selected examples from the recent literature. The molecular recognition of ammonium ions in amino acids is included and the enantioselective binding of chiral ammonium ions by synthetic receptors is also covered. In our conclusion we compare the strengths and weaknesses of the different types of ammonium ion receptors which may help to select the best approach for specific applications.

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Complexation of cyclic dodecadepsipeptide, Cereulide with ammonium salts

Cited by 20 publications

References 7 publications

Rapid synthesis of cyclic oligomeric depsipeptides with positional, stereochemical, and macrocycle size distribution control

Rapid synthesis of cyclic oligomeric depsipeptides with positional, stereochemical, and macrocycle size distribution control

Quantitative Analysis of Cereulide, an Emetic Toxin of Bacillus cereus, by Using Rat Liver Mitochondria

Molecular recognition of organic ammonium ions in solution using synthetic receptors

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