Dataset Information

Synthesis and Applications of Cinchona Squaramide-Modified Poly(Glycidyl Methacrylate) Microspheres as Recyclable Polymer-Grafted Enantioselective Organocatalysts.

ABSTRACT: This work presents the immobilization of cinchona squaramide organocatalysts on poly(glycidyl methacrylate) solid supports. Preparation of the well-defined monodisperse polymer microspheres was facilitated by comprehensive parameter optimization. By exploiting the reactive epoxy groups of the polymer support, three amino-functionalized cinchona derivatives were immobilized on this carrier. To explore the effect of the amino linker, these structurally varied precatalysts were synthesized by modifying the cinchona skeleton at different positions. The catalytic activities of the immobilized organocatalysts were tested in the Michael addition of pentane-2,4-dione and trans-?-nitrostyrene with excellent yields (up to 98?%) and enantioselectivities (up to 96?%?ee). Finally, the catalysts were easily recovered five times by centrifugation without loss of activity.

SUBMITTER: Nagy S

PROVIDER: S-EPMC7702047 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Publications

Synthesis and Applications of Cinchona Squaramide-Modified Poly(Glycidyl Methacrylate) Microspheres as Recyclable Polymer-Grafted Enantioselective Organocatalysts.

Nagy Sándor S Fehér Zsuzsanna Z Kárpáti Levente L Bagi Péter P Kisszékelyi Péter P Koczka Béla B Huszthy Péter P Pukánszky Béla B Kupai József J

Chemistry (Weinheim an der Bergstrasse, Germany) 20200923 59

This work presents the immobilization of cinchona squaramide organocatalysts on poly(glycidyl methacrylate) solid supports. Preparation of the well-defined monodisperse polymer microspheres was facilitated by comprehensive parameter optimization. By exploiting the reactive epoxy groups of the polymer support, three amino-functionalized cinchona derivatives were immobilized on this carrier. To explore the effect of the amino linker, these structurally varied precatalysts were synthesized by modif ...[more]

PMID: 32697895

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Project description:This study aimed to develop poly (vinyl alcohol) grafted glycidyl methacrylate/cellulose nanofiber (PVA-g-GMA/CNF) injectable hydrogels for meniscus tissue engineering. PVA-g-GMA is an interesting polymer for preparing cross-linking injectable hydrogels with UV radiation, but it has poor mechanical properties and low cell proliferation. In this study, CNF as a reinforcing agent was selected to improve mechanical properties and cell proliferation in PVA-g-GMA injectable hydro-gels. The effect of CNF concentration on hydrogel properties was investigated. Both PVA-g-GMA and PVA-g-GMA hydrogels incorporating 0.3, 0.5, and 0.7% (w/v) CNF can be formed by UV curing at a wavelength of 365 nm, 6 mW/cm2 for 10 min. All hydrogels showed substantial microporosity with interconnected tunnels, and a pore size diameter range of 3-68 µm. In addition, all hydrogels also showed high physicochemical properties, a gel fraction of 81-82%, porosity of 83-94%, water content of 73-87%, and water swelling of 272-652%. The water content and swelling of hydrogels were increased when CNF concentration increased. It is worth noting that the reduction of porosity in the hydrogels occurred with increasing CNF concentration. With increasing CNF concentration from 0.3% to 0.7% (w/v), the compressive strength and compressive modulus of the hydrogels significantly increased from 23 kPa to 127 kPa and 27 kPa to 130 kPa, respectively. All of the hydrogels were seeded with human cartilage stem/progenitor cells (CSPCs) and cultured for 14 days. PVA-g-GMA hydrogels incorporating 0.5% and 0.7% (w/v) CNF demonstrated a higher cell proliferation rate than PVA-g-GMA and PVA-g-GMA hydrogels incorporating 0.3% (w/v) CNF, as confirmed by MTT assay. At optimum formulation, 10%PVA-g-GMA/0.7%CNF injectable hydrogel met tissue engineering requirements, which showed excellent properties and significantly promoted cell proliferation, and has a great potential for meniscus tissue engineering application.

Dataset Information

Synthesis and Applications of Cinchona Squaramide-Modified Poly(Glycidyl Methacrylate) Microspheres as Recyclable Polymer-Grafted Enantioselective Organocatalysts.

Publications

Synthesis and Applications of Cinchona Squaramide-Modified Poly(Glycidyl Methacrylate) Microspheres as Recyclable Polymer-Grafted Enantioselective Organocatalysts.

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