Dataset Information

Electron-transfer-initiated benzoin- and Stetter-like reactions in packed-bed reactors for process intensification.

ABSTRACT: A convenient heterogeneous continuous-flow procedure for the polarity reversal of aromatic ?-diketones is presented. Propaedeutic batch experiments have been initially performed to select the optimal supported base capable to initiate the two electron-transfer process from the carbamoyl anion of the N,N-dimethylformamide (DMF) solvent to the ?-diketone and generate the corresponding enediolate active species. After having identified the 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine on polystyrene (PS-BEMP) as the suitable base, packed-bed microreactors (pressure-resistant stainless-steel columns) have been fabricated and operated to accomplish the chemoselective synthesis of aroylated ?-hydroxy ketones and 2-benzoyl-1,4-diones (benzoin- and Stetter-like products, respectively) with a good level of efficiency and with a long-term stability of the packing material (up to five days).

SUBMITTER: Zaghi A

PROVIDER: S-EPMC5238549 | biostudies-other | 2016

REPOSITORIES: biostudies-other

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Electron-transfer-initiated benzoin- and Stetter-like reactions in packed-bed reactors for process intensification.

Zaghi Anna A Ragno Daniele D Di Carmine Graziano G De Risi Carmela C Bortolini Olga O Giovannini Pier Paolo PP Fantin Giancarlo G Massi Alessandro A

Beilstein journal of organic chemistry 20161213

A convenient heterogeneous continuous-flow procedure for the polarity reversal of aromatic α-diketones is presented. Propaedeutic batch experiments have been initially performed to select the optimal supported base capable to initiate the two electron-transfer process from the carbamoyl anion of the N,N-dimethylformamide (DMF) solvent to the α-diketone and generate the corresponding enediolate active species. After having identified the 2-tert-butylimino-2-diethylamino-1,3-d ...[more]

PMID: 28144342

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Project description:One of the main issues when orally administering microorganism-based probiotics is the significant loss of bioactivity as they pass through the gastrointestinal (GI) tract. To overcome these issues, here, we propose to encapsulate the probiotic yeast Kluyveromyces lactis on chemically crosslinked gelatin hydrogels as a means to protect the bioactive agents in different environments. Hydrogels were prepared by the chemical crosslinking of gelatin, which is commercially available and inexpensive. This is crucial to ensure scalability and cost-effectiveness. To explore changes in key physicochemical parameters and their impact on cell viability, we varied the concentration of the crosslinking agent (glutaraldehyde) and the gelatin. The synthesized hydrogels were characterized in terms of morphological, physical-chemical, mechanical, thermal and rheological properties. This comprehensive characterization allowed us to identify critical parameters to facilitate encapsulation and enhance cell survival. Mainly due to pore size in the range of 5-10 μm, sufficient rigidity (breaking forces of about 1 N), low brittleness and structural stability under swelling and relatively high shear conditions, we selected hydrogels with a high concentration of gelatin (7.5% (w/v)) and concentrations of the crosslinking agent of 3.0% and 5.0% (w/w) for cell encapsulation. Yeasts were encapsulated with an efficiency of about 10% and subsequently tested in bioreactor operation and GI tract simulated media, thereby leading to cell viability levels that approached 95% and 50%, respectively. After testing, the hydrogels' firmness was only reduced to half of the initial value and maintained resistance to shear even under extreme pH conditions. The mechanisms underlying the observed mechanical response will require further investigation. These encouraging results, added to the superior structural stability after the treatments, indicate that the proposed encapsulates are suitable to overcome most of the major issues of oral administration of probiotics and open the possibility to explore additional biotech applications further.

Dataset Information

Electron-transfer-initiated benzoin- and Stetter-like reactions in packed-bed reactors for process intensification.

Publications

Electron-transfer-initiated benzoin- and Stetter-like reactions in packed-bed reactors for process intensification.

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