An efficient continuous flow process for the synthesis of a non-conventional mixture of fructooligosaccharides

Zambelli, Paolo; Tamborini, Lucia; Cazzamalli, Samuele; Pinto, Andrea; Arioli, Stefania; Balzaretti, Silvia; Plou, Francisco J.; Fernández‐Arrojo, Lucía; Molinari, Francesco; Conti, Paola; Romano, Diego

doi:10.1016/j.foodchem.2015.06.002

Cited by 44 publications

(41 citation statements)

References 33 publications

(36 reference statements)

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“…The combination of biocatalysis and flow reactor technology can be considered as an enabling methodology intrinsically compatible with the principles of green chemistry . Flow‐based biocatalysis was recently applied for peptide condensation, hydrolysis and formation of esters and sugars, stereoselective carbonyl reduction, formation of C−C bonds, production of nucleosides, monosaccharides, and oligosaccharides, and interconversion of carbonyls and amines using transaminases…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient Oxidation of Amines to Aldehydes with Flow‐based Biocatalysis

et al. 2017

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A new mild and efficient process for the aqueous preparation of aldehydes, which are employed as flavour and fragrance components in food, beverage, cosmetics, as well as in pharmaceuticals, was developed using a continuous‐flow approach based on an immobilised pure transaminase‐packed bed reactor. HEWT, an ω‐transaminase from the haloadapted bacterium Halomonas elongata, has been selected for its excellent stability and substrate scope. Sixteen different amines were rapidly (3–15 min) oxidised to the corresponding aldehydes (90 to 99 %) with only 1 to 5 equivalents of sodium pyruvate. The process was fully automated, allowing for the in‐line recovery of the pure aldehydes (chemical purity >99 % and isolated yields above 80 %), without any further work‐up procedure.

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Section: Introductionmentioning

confidence: 99%

Highly Efficient Oxidation of Amines to Aldehydes with Flow‐based Biocatalysis

et al. 2017

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“…First, commercially available diol 1 (1 g L −1 in 20 m m acetate buffer, pH 6) was successfully oxidized with dried alginate beads of Acetobacter aceti MIM 2000/28 with high enantio‐ and regioselectivity. The immobilized cells were prepared according to a protocol recently reported by us, packed into a glass column (inner diameter 15 mm) and swelled by flowing buffer through the column until their volume tripled. No release of catalyst in the exiting flow stream was observed.…”

Section: Resultsmentioning

confidence: 99%

“…Gel beads were prepared by ionotropic gelation, by following a protocol previously developed by us: a 4 % ( w / v ) sodium alginate solution was prepared in distilled water and stirred until a homogeneous clear solution was formed. The solution was allowed to settle for 2 h in order to eliminate the air bubbles.…”

Section: Methodsmentioning

confidence: 99%

“…The oxidation was performed using Acetobacter aceti MIM 2000/28; this strain is able to completely convert the substrate into ( R )‐3‐hydroxy‐2‐methylpropanoic acid ( 2 ) with an excellent ee (96–97 %) using a conventional batch‐mode biotransformation. To exploit all the advantages of performing (bio)catalyzed reactions in flow, in particular the high local concentration of the biocatalyst, A. aceti has been immobilized as dried alginate‐entrapped cells, that are economical, easy to prepare and can be efficiently used in a packed bed column . Also, importantly, the use of whole cells in biocatalytic oxidation has the great advantage of not requiring an additional cofactor regeneration system.…”

Section: Introductionmentioning

confidence: 99%

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Chemoenzymatic Synthesis in Flow Reactors: A Rapid and Convenient Preparation of Captopril

et al. 2017

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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.

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“…Aldolases [10], amidases [11], transaminases [12], oxidases [13,14], peroxidases [15] are some enzymes that have been successfully applied to a continuous-flow approach. Additionally, lipase-mediated esterification [16][17][18][19][20][21], interesterification [22,23], transesterification [24][25][26] and enzymatic kinetic resolution (EKR) of racemic compounds [27][28][29][30][31][32], have demonstrated the potential of combining continuous-flow systems and biocatalysis.…”

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confidence: 99%

Biocatalysis in continuous-flow mode: A case-study in the enzymatic kinetic resolution of secondary alcohols via acylation and deacylation reactions mediated by Novozym 435®

Thomas¹,

Burich²,

Bandeira³

et al. 2017

Biocatalysis

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Enzymatic kinetic resolution reactions are a well-established way to achieve optically active compounds. When enzymatic reactions are combined to continuous-flow methodologies, other benefits are added, including reproducibility, optimized energy use, minimized waste generation, among others. In this context, we herein report a case study involving lipase-mediated transesterification by acylation and deacylation reactions of secondary alcohols/esters in batch and continuous-flow modes. Acylation reactions were performed with high values of enantiomeric excess (72 up to >99%) and enantioselectivity (E > 200) for both batch and continuous-flow modes. On the other hand, for deacylation reactions using n-butanol as nucleophile, enatiomeric excess ranged between 38 to >99% and E from 6 to >200 were observed for batch mode. For deacylation reactions in continuous-flow mode, results were disappointing, as in some cases, very low or no conversion was observed. Enantiomeric excess ranged from 16 to >99% and enantioselectivity from 5 to >200 were observed. In terms of productivity, continuous-flow mode reactions were superior in both strategies (acylation: r from 1.1 up to 18.1-fold higher, deacylation: 2.8 up to 7.4- fold higher in continuous-flow than in batch mode).

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An efficient continuous flow process for the synthesis of a non-conventional mixture of fructooligosaccharides

Cited by 44 publications

References 33 publications

Highly Efficient Oxidation of Amines to Aldehydes with Flow‐based Biocatalysis

Highly Efficient Oxidation of Amines to Aldehydes with Flow‐based Biocatalysis

Chemoenzymatic Synthesis in Flow Reactors: A Rapid and Convenient Preparation of Captopril

Biocatalysis in continuous-flow mode: A case-study in the enzymatic kinetic resolution of secondary alcohols via acylation and deacylation reactions mediated by Novozym 435®

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