Synthesis of the host-selective plant toxins AF IIa, AF IIc and AKII, employing sharpless chiral epoxidation under kinetic control

Crombie, Leslie; Jarrett, Sandra R. M.

doi:10.1016/s0040-4039(01)80716-4

Cited by 7 publications

References 15 publications

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Asymmetric Epoxidation of Allylic Alcohols: the Katsuki–Sharpless Epoxidation Reaction

1996

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In 1980, Sharpless and Katsuki discovered a system for the asymmetric epoxidation of primary allylic alcohols that utilizes Ti(OPr‐ i ) 4 , a dialkyl tartrate as a chiral ligand, and tert ‐butyl hydroperoxide as the oxidant. Notably, this reaction exhibits high levels of enantioselectivity (usually > 90% ee). Like other metal‐catalyzed epoxidations, this reaction also proceeds under mild conditions with good chemical yield and with high regio‐ and chemoselectivity. Various aspects of this reaction, including its mechanism, early synthetic applications, and further transformations of the epoxy alcohol product, have been reviewed. In this chapter, the full scope and limitations of this reaction, its synthetic applications, and typical experimental conditions are described.

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Asymmetric Epoxidation of Allylic Alcohols: the Katsuki–Sharpless Epoxidation Reaction

1996

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A Chemical Approach for Elucidating the Molecular Interaction of Host-Specific AK-Toxin with Japanese Pear

Miyagawa

Okada

Uemura

et al. 2002

Advances in Microbial Toxin Research and Its Biotechnological Exploitation

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Host recognition by toxigenic plant pathogens

1991

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Certain fungal pathogens release host-selective (or host-specific) toxins (HST) as a host recognition factor during spore germination at the infection site on plants. Prior to penetration of the pathogen into its host, the released toxin specifically binds to a putative receptor on the host cells and initiates signaling mechanisms leading to pleiotropic effects on cells. Of these, the crucial one negates the general and inducible defense reactions of the cells. This is accomplished by a signal from the HST, which is transduced through a path way at or near the step of plasma membrane modulation, which is directly or indirectly triggered by the HST. This mechanism operates even though the toxin may affect mitochondria or chloroplasts as the primary target organelle. The fungal spore is able to penetrate the so-called 'narcotized cell' and completes the initial colonization of the host. The host recognition process may take place without necessitating host cell death, even in the case of perthophytic parasites. At the molecular level, HST-mediated recognition of the host by a pathogen requires strict stereochemical precision like a lock and key.

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Synthesis of the host-selective plant toxins AF IIa, AF IIc and AKII, employing sharpless chiral epoxidation under kinetic control

Cited by 7 publications

References 15 publications

Asymmetric Epoxidation of Allylic Alcohols: the Katsuki–Sharpless Epoxidation Reaction

Asymmetric Epoxidation of Allylic Alcohols: the Katsuki–Sharpless Epoxidation Reaction

A Chemical Approach for Elucidating the Molecular Interaction of Host-Specific AK-Toxin with Japanese Pear

Host recognition by toxigenic plant pathogens

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