Methyl allyl ether formation in plants: novel S-adenosyl
A novel 41 kDa methyltransferase displaying high regiospecificity towards the allylic hydroxyl moiety of coniferyl alc. was cloned from suspension cultures of Linum nodiflorum L. and expressed in E. coli. The apparent Km for coniferyl alc. is 7.23 μM with a Vmax of 707.5 pkat mg-1 protein at 30°, whereas the Km for the co-substrate S-adenosyl-l-methionine is 18.5 μM. Structure-function relationship studies revealed stringent structure requirements. Even minor substructure deviations as the side-chain saturation or changes in the Ph ring substitution result in activities decreased by 75-90%. Crotyl and allyl alcs. are not substrates, confirming that the aromatic ring itself is indispensable, and solely the derivatives with a C3 side-chain are accepted. The enzyme shares only similarities under 46% on amino acid level with other known methyltransferases. The designated reaction product, coniferyl alc. 9-Me ether, could be detected in suspension cells. The highest content of up to 0.02% of the dry mass is concurrent with an increase of the specific enzyme activity that reaches its maximum of 3.94 pkat mg-1 on day 6 of the culture period. Transcript levels estimated by semi-quant. RT-PCR remain constant until day 6 and recede thereafter. The corresponding methyltransferase from Linum flavum L. differs mainly by one short variable fragment. Biochem. characterization revealed a higher catalytic efficiency and a slightly broader substrate plasticity together with a lower sensitivity to the presence of Zn2+, Cu2+ and Co2+. This is to our knowledge the first report of a regiospecific allylic O-methylation of phenylpropanoids in plants. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Product Details of 3929-47-3).
3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. Ethyl ether is an excellent solvent for extractions and for a wide variety of chemical reactions. It is also used as a volatile starting fluid for diesel engines and gasoline engines in cold weather. Dimethyl ether is used as a spray propellant and refrigerant. Methyl t-butyl ether (MTBE) is a gasoline additive that boosts the octane number and reduces the amount of nitrogen-oxide pollutants in the exhaust. The ethers of ethylene glycol are used as solvents and plasticizers.Product Details of 3929-47-3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem