Synthetic studies on (+)-hydantocidin (1): A total synthesis of (+)-hydantocidin, a new herbicidal metabolite from microorganism

Mio, Shigeru; Ichinose, Reiji; Goto, Kuniko; Sugai, Soji; Sato, Sadao

doi:10.1016/s0040-4020(01)96122-8

Cited by 77 publications

(19 citation statements)

References 23 publications

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“…Its intriguing structure and remarkable biological properties have stimulated a considerable amount of synthetic work on the parent compound (9)(10)(11)(12)(13)(14) and its analogues (15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25). The novel injury symptoms it elicits in plants has prompted a detailed investigation of its mode of action.…”

mentioning

confidence: 99%

The mode of action and the structure of a herbicide in complex with its target: binding of activated hydantocidin to the feedback regulation site of adenylosuccinate synthetase.

Fonné‐Pfister

Chemla

Ward

et al. 1996

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

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(+)-Hydantocidin, a recently discovered natural spironucleoside with potent herbicidal activity, is shown to be a proherbicide that, after phosphorylation at the 5' position, inhibits adenylosuccinate synthetase, an enzyme involved in de novo purine synthesis. The mode of binding of hydantocidin 5'-monophosphate to the target enzyme was analyzed by determining the crystal structure of the enzyme-inhibitor complex at 2.6-A resolution. It was found that adenylosuccinate synthetase binds the phosphorylated compound in the same fashion as it does adenosine 5'-monophosphate, the natural feedback regulator of this enzyme. This work provides the first crystal structure of a herbicide-target complex reported to date.

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mentioning

confidence: 99%

The mode of action and the structure of a herbicide in complex with its target: binding of activated hydantocidin to the feedback regulation site of adenylosuccinate synthetase.

Fonné‐Pfister

Chemla

Ward

et al. 1996

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

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“…Hydantocidin ( Figure 2) is a relatively new patented herbicide from Streptomyces hygroscopicus (59,61,62). Hydantocidin is highly effective as a herbicide against both monocotyledonous and dicotyledonous weeds.…”

Section: Phytotoxins From Microbesmentioning

confidence: 99%

Natural Products with Potential Use as Herbicides

Duke

Abbas

1994

ACS Symposium Series

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There is great incentive to discover effective and economically feasible herbicides that are toxicologically and environmentally benign.Several hundred active ingredients of herbicides are now sold world-wide. Virtually all of these compounds were discovered by screening compounds from organic chemical synthesis programs.Leads for the structure of one group of patented herbicides came from 1,8-cineole, a well known plant allelochemical. However, plants have thus far not been as lucrative as microbial products as a source of phytotoxic compounds with the potential for direct use as herbicides or as templates for new synthetic herbicide classes. Microbial phytotoxins have provided valuable information on potential molecular target sites for herbicides. This information has also been useful in probing the biochemistry of plants. Phosphinothricin (glufosinate when synthetic), a product of Streptomyces viridochromogenes, is a successful herbicide that is environmentally and toxicologically benign. Bialaphos, a tripeptide from S. hygroscopicus which degrades to phosphinothricin in target plants, is the only commercial herbicide produced by biosynthesis. Many other microbial products have been patented as herbicides and some of these are under active development.Most of these compounds are from non-plant pathogens; however, there is growing interest in utilizing plant pathogens as sources of herbicide leads. Tentoxin, cornexistin, and AAL-toxin are discussed in detail as examples of microbial toxins with the potential for herbicide development. An overview of natural phytotoxins that have been considered for herbicides is provided, as well as considerations of the pesticide industry in using this approach. This chapter not subject to U.S.

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“…Aplysinopsins are isolated from marine organisms, and they exhibit cytotoxicity to cancer cells and ability to affect neurotransmitters [35][36][37]. Other hydantoin derivatives also exhibit a broad range of biological activities in medicinal (antitumor, anticovulsant, antimuscarinic, antiulcer, and antiarrythmic) [38][39][40][41][42] and agrochemical (herbicidal and fungicidal) [43][44][45][46][47][48][49] applications. In addition to solution phase synthesis [50][51], solid-phase synthesis of hydantoin has also been reported in the literature [52][53][54][55][56].…”

Section: Introductionmentioning

confidence: 99%

Fluorous parallel synthesis of a hydantoin/thiohydantoin library

Zhang

2005

Mol Divers

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Fluorous tagging strategy is applied to solution-phase parallel synthesis of a library containing hydantoin and thiohydantoin analogs. Two perfluoroalkyl (Rf)-tagged α-amino esters each react with 6 aromatic aldehydes under reductive amination conditions. Twelve amino esters then each react with 10 isocyanates and isothiocyanates in parallel. The resulting 120 ureas and thioureas undergo spontaneous cyclization to form the corresponding hydantoins and thiohydantoins. The intermediate and final product purifications are performed with solid-phase extraction (SPE) over FluoroFlash™ cartridges, no chromatography is required. Using standard instruments and straightforward SPE technique, one chemist accomplished the 120-member library synthesis in less than 5 working days, including starting material synthesis and product analysis.

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Synthetic studies on (+)-hydantocidin (1): A total synthesis of (+)-hydantocidin, a new herbicidal metabolite from microorganism

Cited by 77 publications

References 23 publications

The mode of action and the structure of a herbicide in complex with its target: binding of activated hydantocidin to the feedback regulation site of adenylosuccinate synthetase.

The mode of action and the structure of a herbicide in complex with its target: binding of activated hydantocidin to the feedback regulation site of adenylosuccinate synthetase.

Natural Products with Potential Use as Herbicides

Fluorous parallel synthesis of a hydantoin/thiohydantoin library

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