Efficient and convenient synthesis of 1-methylcyclopropene

Magid, Ronald M.; Clarke, Thomas C.; Duncan, Charles D.

doi:10.1021/jo00808a041

Cited by 47 publications

(15 citation statements)

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“…1-MCP was prepared (Magid et al, 1971) and stored in the gas phase in a container with saturated (NH 4 ) 2 SO 4 as a seal. Concentration was determined by gas chromatography using a column of Carbopak B (80/120 mesh size), 3% (v/v) SP1500 (Supelco) with butane as the calibration standard.…”

Section: Preparation and Use Of 1-mcpmentioning

confidence: 99%

Ethylene Perception by the ERS1 Protein in Arabidopsis

et al. 2000

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Ethylene perception in Arabidopsis is controlled by a family of five genes, including ETR1, ERS1 (ethylene response sensor 1), ERS2, ETR2, and EIN4. ERS1, the most highly conserved gene with ETR1, encodes a protein with 67% identity to ETR1. To clarify the role of ERS1 in ethylene sensing, we biochemically characterized the ERS1 protein by heterologous expression in yeast. ERS1, like ETR1, forms a membrane-associated, disulfide-linked dimer. In addition, yeast expressing the ERS1 protein contains ethylene-binding sites, indicating ERS1 is also an ethylene-binding protein. This finding supports previous genetic evidence that isoforms of ETR1 also function in plants as ethylene receptors. Further, we used the ethylene antagonist 1-methylcyclopropene (1-MCP) to characterize the ethylene-binding sites of ERS1 and ETR1. We found 1-MCP to be both a potent inhibitor of the ethylene-induced seedling triple response, as well as ethylene binding by yeast expressing ETR1 and ERS1. Yeast expressing ETR1 and ERS1 showed nearly identical sensitivity to 1-MCP, suggesting that the ethylene-binding sites of ETR1 and ERS1 have similar affinities for ethylene.

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Section: Preparation and Use Of 1-mcpmentioning

confidence: 99%

Ethylene Perception by the ERS1 Protein in Arabidopsis

et al. 2000

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“…Methylenecyclopropane was obtained from Fluka Chemical Company, Ronkonkoma, New York, 11779-7238, USA and I-methylcyclopropene was synthesised as previously described [6,8].…”

Section: Chemicalsmentioning

confidence: 99%

“…In order to label the ethylene receptor, I-MCP [8] was labelled with tritium and the specific activity obtained was 60 mCi mmol-1 . Diffusion of the compound from the tissues was studied on carnations.…”

Section: Diffusion Of3 H I-mep On Carnation Petalsmentioning

confidence: 99%

Effect of 1-methylcyclopropene and methylenecyclopropane on ethylene binding and ethylene action on cut carnations

Sisler

Dupille

Serek³

1996

Plant Hormone Signal Perception and Transduction

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1-Methy1cyclopropene (l-MCP), formerly designated as Sis-X, has been shown to be an effective inhibitor of ethylene responses in carnation flowers in either the light or the dark. The binding appears to be to the receptor and to be "permanent". A 6 h treatment at 2.5 nll-1 is sufficient to protect against ethylene, and 0.5 nll-1 is sufficient if exposure is for 24 h. As carnation flowers age, a little higher concentration appears to be needed. Most of the natural increase in ethylene production during senescence is prevented by treatment with 1-MCP. A closely related compound, methylenecyclopropane shows ethylene activity. A tritium labelled 1-MCP (60 mCi mmol-1 ) has been prepared. A higher specific activity is needed for more critical studies.

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“…In the appropriate containers, small beakers containing 20% KOH and/or 0.25 M Hg(ClO 4 ) 2 were included to absorb CO 2 and ethylene respectively, released by the fruit (Liu et al, 1985). The 1-MCP used was synthesized according to the method of Magid et al (1971) as a stable lithium derivative in ether solution and stored at -20°C until use. Intact fruit were enclosed in 10 L glass jars fitted with a silicon rubber stopper.…”

Section: Treatments With Exogeneous Ethylene Co 2 and 1-mcpmentioning

confidence: 99%

Expression of a 1-aminocyclopropane-1-carboxylate (ACC) oxidase gene in peach (Prunus persica L.) fruit in response to treatment with carbon dioxide and 1-methylcyclopropene: possible role of ethylene

Mathooko¹,

Tsunashima²,

Kubo³

et al. 2004

Afr. J. Biotechnol.

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In this study we investigated the effect of exogenous ethylene treatment on ethylene production, 1aminocyclopropane-1-carboxylate (ACC) oxidase activity and expression of an ACC oxidase (PP-ACO1) gene previously cloned (Mathooko et al., 2001) in peach (Prunus persica L.) fruit. We also investigated the mode of action of CO 2 and 1-methycyclopropene (1-MCP) in the regulation of ethylene biosynthesis during peach fruit ripening. Fruits were treated with various concentrations of ethylene (0.1, 1, 10, 100, 500, 1000 ppm) and also with CO 2 and 1-MCP in the presence or absence of 500 ppm ethylene. Ethylene stimulated ethylene production at concentrations of 100 ppm and above while ACC oxidase activity was stimulated in a concentration-dependent manner. PP-ACO1 was slightly constitutively expressed and exogenous ethylene stimulated accumulation of its mRNA transcript in a concentration-dependent manner up to 100 ppm after which the level remained constant. CO 2 and 1-MCP inhibited the ethylenestimulated ethylene production, ACC oxidase activity and accumulation of PP-ACO1 transcripts by about 50%. These results indicate that ethylene plays a key role in the regulation of ethylene production and ACC oxidase activity and its gene expression in peach fruit. Further the results indicate that CO 2 and 1-MCP regulate ethylene biosynthesis in peach fruit during ripening, at least in part, by antagonizing ethylene action.

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Efficient and convenient synthesis of 1-methylcyclopropene

Cited by 47 publications

References 0 publications

Ethylene Perception by the ERS1 Protein in Arabidopsis

Ethylene Perception by the ERS1 Protein in Arabidopsis

Effect of 1-methylcyclopropene and methylenecyclopropane on ethylene binding and ethylene action on cut carnations

Expression of a 1-aminocyclopropane-1-carboxylate (ACC) oxidase gene in peach (Prunus persica L.) fruit in response to treatment with carbon dioxide and 1-methylcyclopropene: possible role of ethylene

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