1910-47-0Relevant articles and documents
Chemoenzymatic Synthesis in Flow Reactors: A Rapid and Convenient Preparation of Captopril
De Vitis, Valerio,Dall'Oglio, Federica,Pinto, Andrea,De Micheli, Carlo,Molinari, Francesco,Conti, Paola,Romano, Diego,Tamborini, Lucia
, p. 668 - 673 (2017)
The chemoenzymatic flow synthesis of enantiomerically pure captopril, a widely used antihypertensive drug, is accomplished starting from simple, inexpensive, and readily available reagents. The first step is a heterogeneous biocatalyzed regio- and stereoselective oxidation of cheap prochiral 2-methyl-1,3-propandiol, performed in flow using immobilized whole cells of Acetobacter aceti MIM 2000/28, thus avoiding the use of aggressive and environmentally harmful chemical oxidants. The isolation of the highly hydrophilic intermediate (R)-3-hydroxy-2-methylpropanoic acid is achieved in-line by using a catch-and-release strategy. Then, three sequential high-throughput chemical steps lead to the isolation of captopril in only 75 min. In-line quenching and liquid–liquid separation enable breaks in the workflow and other manipulations to be avoided.
Enantioselective oxidation of prochiral 2-methyl-1,3-propandiol by Acetobacter pasteurianus
Molinari, Francesco,Gandolfi, Raffaella,Villa, Raffaella,Urban, Eva,Kiener, Andreas
, p. 2041 - 2043 (2003)
The microbial oxidation of prochiral 2-methyl-1,3-propandiol into (R)-3-hydroxy-2-methyl propionic acid with Acetobacter pasteurianus DSM 8937 is reported. The biotransformation was optimised furnishing (R)-3-hydroxy-2-methyl propionic acid with 97% enantiomeric excess and 100% molar conversion of 5 g/L within 2 h. A simple fed-batch procedure allowed for the obtainment of 25 g/L of the enantiomerically enriched acid. (R)-3-Hydroxy-2-methyl propionic acid is an important building block for the synthesis of Captopril, a widely used antihypertensive drug.
Synthesis of Enantiomerically Enriched 2-Hydroxymethylalkanoic Acids by Oxidative Desymmetrisation of Achiral 1,3-Diols Mediated by Acetobacter aceti
Brenna, Elisabetta,Cannavale, Flavia,Crotti, Michele,De Vitis, Valerio,Gatti, Francesco G.,Migliazza, Gaia,Molinari, Francesco,Parmeggiani, Fabio,Romano, Diego,Santangelo, Sara
, p. 3796 - 3803 (2016/12/24)
The stereoselective desymmetrisation of achiral 2-alkyl-1,3-diols is performed by oxidation of one of the two enantiotopic primary alcohol moieties by means of Acetobacter aceti MIM 2000/28 to afford the corresponding chiral 2-hydroxymethyl alkanoic acids (up to 94 % ee). The procedure, carried out in aqueous medium under mild conditions of pH, temperature and pressure, contributes to enlarge the portfolio of enzymatic oxidations available to organic chemists for the development of sustainable manufacturing processes.
Solvent effect and reactivity trend in the aerobic oxidation of 1,3-propanediols over gold supported on titania: Nmr diffusion and relaxation studies
D'Agostino, Carmine,Kotionova, Tatyana,Mitchell, Jonathan,Miedziak, Peter J.,Knight, David W.,Taylor, Stuart H.,Hutchings, Graham J.,Gladden, Lynn F.,Mantle, Mick D.
, p. 11725 - 11732 (2013/09/12)
In recent work, it was reported that changes in solvent composition, precisely the addition of water, significantly inhibits the catalytic activity of Au/TiO2 catalyst in the aerobic oxidation of 1,4-butanediol in methanol due to changes in diffusion and adsorption properties of the reactant. In order to understand whether the inhibition mechanism of water on diol oxidation in methanol is generally valid, the solvent effect on the aerobic catalytic oxidation of 1,3-propanediol and its two methyl-substituted homologues, 2-methyl-1,3-propanediol and 2,2-dimethyl-1,3-propanediol, over a Au/TiO2 catalyst has been studied here using conventional catalytic reaction monitoring in combination with pulsed-field gradient nuclear magnetic resonance (PFG-NMR) diffusion and NMR relaxation time measurements. Diol conversion is significantly lower when water is present in the initial diol/methanol mixture. A reactivity trend within the group of diols was also observed. Combined NMR diffusion and relaxation time measurements suggest that molecular diffusion and, in particular, the relative strength of diol adsorption, are important factors in determining the conversion. These results highlight NMR diffusion and relaxation techniques as novel, non-invasive characterisation tools for catalytic materials, which complement conventional reaction data. In solvent company: The solvent effect on the aerobic catalytic oxidation of 1,3-propanediol and its two methyl-substituted homologues, 2-methyl-1,3-propanediol and 2,2-dimethyl-1,3-propanediol, over a Au/TiO 2 catalyst has been studied. The results show that diol conversion is significantly lower when water is present in the initial diol/methanol mixture. A reactivity trend within the group of diols was also observed. Copyright
