Synthetic studies on (+)-hydantocidin (3): a new synthetic method for construction of the spiro-hydantoin ring at the anomeric position of D-ribofuranose

The site of action of hydantocidin was probed using Arabidopsis fhaliana plants growing on agar plates. Herbicidal effects were reversed when the agar medium was supplemented with AMP, but not IMP or CMP, suggesting that hydantocidin blocked the two-step conversion of IMP to AMP in the de novo purine biosynthesis pathway. Hydantocidin itself did not inhibit adenylosuccinate synthetase or adenylosuccinate lyase isolated from Zea mays. However, a phosphorylated derivative of hydantocidin, N-acetyl-5'-phosphohydantocidin, was a potent inhibitor of the synthetase but not of the lyase. These results identify the site of action of hydantocidin and establish adenylosuccinate synthetase as an herbicide target of commercial potential.

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“…1) was synthesized as described (Mio et al, 1991). NAH' and NAPH' were synthesized by variations of that procedure to be published elsewhere.…”

Section: Materiaismentioning

confidence: 99%

Adenylosuccinate Synthetase: Site of Action of Hydantocidin, a Microbial Phytotoxin

Siehl¹,

Subramanian²,

Walters³

et al. 1996

Plant Physiol.

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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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“…25 Desta forma, a oxidação foi efetuada com tetróxido de rutênio (RuO 4 ), 29 um forte agente oxidante gerado in situ pela combinação de NaIO 4 com quantidades catalíticas de cloreto de rutênio hidratado e de BTEAC como catalisador de transferência de fase 25 (Esquema 4). Embora seja um reagente relativamente caro, o sal de rutênio(III) é empregado em pequenas quantidades (2-3 mol %), o que permite sua utilização sem um aumento considerável dos custos.…”

Section: Esquema 2 Dicetalização Da D-frutoseunclassified

“…Além disso, as condições descritas incluem a necessidade de conduzir ambas as etapas reacionais sob atmosfera inerte, o que é inviável em laboratórios que não dispõem de infraestrutura adequada. Desta forma, decidiu-se revisar as metodologias previamente descritas na literatura para a preparação de 1 a partir de 2 [20][21][22][23][24][25] e, de modo a desenvolver experimentos compatíveis com as condições existentes em nossos laboratórios de ensino, optou-se pela substituição de ácido perclórico e de PCC por reagentes alternativos.…”

Section: Introductionunclassified

Síntese da Epoxone a partir de D-frutose: um experimento didático em laboratório de Química Orgânica com foco nos princípios da Química Verde

Bisol¹,

Marques²,

Rossa³

et al. 2012

Quím. Nova

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Synthetic studies on (+)-hydantocidin (3): a new synthetic method for construction of the spiro-hydantoin ring at the anomeric position of D-ribofuranose

Cited by 128 publications

References 24 publications

Adenylosuccinate Synthetase: Site of Action of Hydantocidin, a Microbial Phytotoxin

Adenylosuccinate Synthetase: Site of Action of Hydantocidin, a Microbial Phytotoxin

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.

Síntese da Epoxone a partir de D-frutose: um experimento didático em laboratório de Química Orgânica com foco nos princípios da Química Verde

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