1211-29-6Relevant articles and documents
Lipase-catalyzed preparation of both enantiomers of methyl jasmonate
Kiyota, Hiromasa,Higashi, Emi,Koike, Takanori,Oritani, Takayuki
, p. 1035 - 1038 (2001)
Preparation of both enantiomeric methyl jasmonates 1 was achieved via lipase-catalyzed resolution of (±)-methyl 7-epicucurbate 3. Lipase P (Amano) provided good selectivity both for acylation of (±)-3 (E = 370) and hydrolysis of the corresponding acetate (E = 41). Resolution of (±)-methyl 6,7-diepicucurbate 2 gave poor results. It was found that the (6R,7S)-configuration was suitable for the selective enzymatic reaction and the C-(3) stereochemistry of the substrate did not influence the enzymatic reaction.
Identification of jasmonic acid and abscisic acid as senescencepromoting substances from Cleyera ochnacea DC
Ueda,Kato
, p. 1975 - 1976 (1982)
-
Investigation of synthetic lipase and its use in transesterification reactions
Kecili, Rustem,Say, Rdvan,Ers?z, Arzu,Hür, Deniz,Denizli, Adil
body text, p. 1981 - 1984 (2012/06/29)
A novel synthetic polymer selective for p-nitrophenylpalmitate was synthesized by molecular imprinting technique. We have combined the principle of molecular imprinting with the ability of histidine, glutamic acid and serine to form a catalytic cavity that can promote the catalytic degradation of p-nitrophenyl palmitate. For the creation of such catalytic sites we first synthesized appropriate monomers and used p-nitrophenyl palmitate as a template to synthesize the imprinted polymers and the binding characteristics of the polymers were evaluated. The optimum pH was determined by evaluating different pH values and the hydrolytic activity of synthetic lipase was evaluated in the framework of Micheaelis-Menten kinetics. In addition, the values of maximal rate: Vm (0.68 mM/min) and Michaelis-Menten constant, Km (1.4 × 10 -2 mM) were obtained from Lineweaver-Burk plots for the imprinted polymeric catalyst.
Asymmetric total synthesis of enantiopure (-)-methyl jasmonate via catalytic asymmetric intramolecular cyclopropanation of α-diazo-β-keto sulfone
Takeda, Hiroyuki,Watanabe, Hideaki,Nakada, Masahisa
, p. 8054 - 8063 (2007/10/03)
A new asymmetric total synthesis of enantiopure (-)-methyl jasmonate is described. This synthesis was accomplished starting from the new enantiopure building block prepared via the catalytic asymmetric intramolecular cyclopropanation (IMCP) of the α-diazo-β-keto 1-naphthyl sulfone, which was devised to give good selectivity both in the IMCP reaction and in the C-alkynylation of the intermediate required for the total synthesis of enantiopure (-)-methyl jasmonate.
Synthesis of (±)-methyl epijasmonate and (±)-methyl dihydroepijasmonate by diastereoselective protonation
Krause, Norbert,Ebert, Sophia
, p. 3837 - 3841 (2007/10/03)
The synthesis of (±)-methyl epijasmonate (1) was carried out by Michael addition of lithium diallylcuprate to enone 3 and diastereoselective enolate protonation with the chelating proton source 2-(methyliminomethyl)phenol (4; 85% ds), followed by ozonolysis, oxidation, esterification, and Lindlar hydrogenation. During the ozonisation, epimerization to the thermodynamically more stable trans-isomer takes place to some extent, so that 1 was isolated with a cis:trans ratio of 72:28. The analogous transformation of enone 7 with lithium diallylcuprate and 2-(methyliminomethyl)phenol (4) furnished ketone 8 with 94% ds; this was then transformed into (±)-methyl dihydroepijasmonate (2) with a cis:trans ratio of 91:9. The olfactory properties of this product are superior to those available from commercial sources.