On the kinetic resolution of sterically hindered myo-inositol derivatives in organic media by lipases

Kinetic resolution of a precursor for myo-inositol phosphates under continuous flow conditions

“…In fact, it is reported that continuous flow systems improve the productivity of the methodology and reduce reaction times. Continuous flow systems are preferred over batch reactors due to their greater process control, high productivity and improvement of product quality/purity and yield [9,10]. Among the different types of continuous-flow reactors, packed-bed reactors (PBR) are the most popular due to their high efficiency, low cost and ease of construction, operation and maintenance [11][12][13][14].…”

“…Recently, we have developed kinetic resolutions of (±)-1,3,6-tri-O-benzil-myo-inositol, (±)-1, and (±)-1,2-O-isopropylidene-3, 6-di-O-benzyl-myo-inositol using lipase B from Candida antarctica (CaLB) with excellent yields and enantiomeric ratios [9,15]. Nevertheless, these procedures suffer from long reaction times.…”

“…The results of this study are reported herein. In the previous investigation on the kinetic resolutions this inositol [9], under catalysis by CaLB in batch conditions, high selectivities were achieved when vinyl acetate, hexane, TBME and, to a lesser extent, ethyl acetate were used as solvents (vinyl acetate as acylating agent).…”

Enantioselective catalysis from Pseudomonas cepacia on the kinetic resolution by different reactors

“…Its success depends on several factors, such as specificity of the biocatalyst, type of immobilization, substrate, solvent, and reactor systems. 1,2 Currently, most of the studies in the literature report the use of reactors in small scale stirred tank on batch system 3 . In this way, the phosphorylated myo-inositols appear as interesting substrates, to be studied due to their potential in the development of new drugs.…”

“…The phosphorylated myo-inositols play key roles in fundamental biological phenomena such as cellular signal transduction. [4][5] The present work aims at the use from immobilized Pseudomonas cepacia lipase on the efficient kinetic resolution of (±)-1,3,6-tri-O-benzilmyo-inositol (mio-I) 1 , a precursor known of 1D-2,4,5-myo-inositol trisphosphate 4 , a bioactive substance and a potential one for other inositol bisphosphates and trisphosphates. The biocatalytic continuous flow process and the batch process by alcoholysis reaction were investigated (Figure 1).…”