The herbicide flamprop‐M‐methyl has a new antimicrotubule mechanism of action

Tresch, Stefan; Niggeweg, Ricarda; Großmann, Klaus

doi:10.1002/ps.1618

Cited by 12 publications

(5 citation statements)

References 13 publications

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“…As a further demonstration of its synthetic utility, we used the copper-catalyzed asymmetric N–H insertion reaction to prepare the chiral arylalanine herbicide ( R )-flamprop-M-isopropyl . The reaction of isopropyl α-diazopropionate ( 4n ) with 3-chloro-4-fluoroaniline ( 5l ) catalyzed by 1 mol % Cu–( S a , S , S )- 1 afforded insertion product 6y in 97% yield with 98% ee.…”

Section: Resultsmentioning

confidence: 99%

Well-Defined Binuclear Chiral Spiro Copper Catalysts for Enantioselective N–H Insertion

et al. 2011

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An asymmetric N-H insertion of α-diazoesters with anilines catalyzed by well-defined copper complexes of chiral spiro bisoxazoline ligands was studied in detail. The copper-catalyzed asymmetric N-H insertion of a wide range of α-alkyl-α-diazoacetates with anilines was accomplished with excellent enantioselectivity (up to 98% ee) and provided an efficient method for the preparation of optically active α-amino acid derivatives. A correlation study of the electronic properties of the substrates with the enantioselectivity of the N-H insertion reaction supports a stepwise insertion mechanism, and the significant first-order kinetic isotope effect proves that the proton transfer is most likely the rate-limiting step. A binuclear chiral spiro copper catalyst having 14-electron copper centers, a trans coordination model, a perfect C(2)-symmetric chiral pocket, and significant Cu-Cu interaction was isolated and extensively studied. The novel structure of the binuclear chiral spiro copper catalyst leads to unique reactivity as well as enantioselectivity in the N-H insertion reaction.

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Section: Resultsmentioning

confidence: 99%

Well-Defined Binuclear Chiral Spiro Copper Catalysts for Enantioselective N–H Insertion

et al. 2011

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“…By contrast the microtubuledepolymerizing herbicide ethyl-N-phenylcarbamate (EPC) seems to occupy a different binding site on tubulin dimers compared to oryzalin and as a result, EPC-resistant lines of rice remain susceptible to oryzalininduced microtubule depolymerization (Morettini et al, 2013). Finally, it is noteworthy that the herbicide flamprop-M-methyl disrupts microtubule organization of mitotic and cytokinetic arrays (mitotic spindles and phragmoplasts) without affecting microtubule integrity and without disturbing the arrangement of interphase cortical microtubule arrays, prompting the elucidation of its mechanism of function (Tresch et al, 2008).…”

Section: Importance Of Cytoskeletal Elements In Abiotic Stress Responmentioning

confidence: 97%

Biotechnological aspects of cytoskeletal regulation in plants

Komis

Luptovčiak

Doskočilová

et al. 2015

Biotechnology Advances

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“…Citral, a monoterpene, has been reported to primarily affect mitotic MTs rather than cortical MTs (Chaimovitsh et al, 2012). In contrast, flamprop-M-methyl is an anti-microtubular drug that, although ineffective on MT polymerization, severely affects the orientation of the MTs that are part of the spindle and the phragmoplast arrays, thereby causing minus-end disassembly (Tresch et al, 2008).…”

Section: Tubulin and Drugsmentioning

confidence: 99%

Multiple tubulins: evolutionary aspects and biological implications

2013

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SUMMARYPlant tubulin is a dimeric protein that contributes to formation of microtubules, major intracellular structures that are involved in the control of fundamental processes such as cell division, polarity of growth, cell-wall deposition, intracellular trafficking and communications. Because it is a structural protein whose function is confined to the role of microtubule formation, tubulin may be perceived as an uninteresting gene product, but such a perception is incorrect. In fact, tubulin represents a key molecule for studying fundamental biological issues such as (i) microtubule evolution (also with reference to prokaryotic precursors and the formation of cytomotive filaments), (ii) protein structure with reference to the various biochemical features of members of the FstZ/tubulin superfamily, (iii) isoform variations contributed by the existence of multi-gene families and various kinds of post-translational modifications, (iv) anti-mitotic drug interactions and mode of action, (v) plant and cell symmetry, as determined using a series of tubulin mutants, (vi) multiple and sophisticated mechanisms of gene regulation, and (vii) intron molecular evolution. In this review, we present and discuss many of these issues, and offer an updated interpretation of the multi-tubulin hypothesis.

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The herbicide flamprop‐M‐methyl has a new antimicrotubule mechanism of action

Abstract: The results indicate that flamprop-M-methyl is a mitotic disrupter herbicide with a new antimicrotubule mechanism of action that affects orientation of spindle and phragmoblast microtubules, possibly by minus-end microtubule disassembly.

Cited by 12 publications

References 13 publications

Well-Defined Binuclear Chiral Spiro Copper Catalysts for Enantioselective N–H Insertion

Well-Defined Binuclear Chiral Spiro Copper Catalysts for Enantioselective N–H Insertion

Biotechnological aspects of cytoskeletal regulation in plants

Multiple tubulins: evolutionary aspects and biological implications

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