Stereoselective synthesis of (+)-hydantocidin

Chemla, Philippe

doi:10.1016/s0040-4039(00)60134-x

Cited by 57 publications

(15 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 is highly effective as a herbicide against both monocotyledonous and dicotyledonous weeds. Its low fermentation yield has resulted in development of synthetic procedures that give good yields (59,(62)(63)(64). It is non-selective and, thus, could only be used selectively with crops if the crops can be genetically engineered to be resistant, as been done with other non-selective herbicides (21).…”

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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“…It is possible that a chemotherapeutic approach to the treatment of diseases induced by mycobacteria, such as tuberculosis and leprosy, would be to find compounds which inhibit either the biosynthesis of Tdp-rhamnose or its subsequent incorporation into the cell wall. The term spironucleoside was introduced in 1990 to designate a class of spiranic sugar derivatives in which the anomeric carbon belongs to both the sugar ring and to a heterocyclic base [4-6]. …”

Section: Introductionmentioning

confidence: 99%