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Microwave-Assisted Synthesis of 5'-O-methacryloylcytidine Using the Immobilized Lipase Novozym 435.

ABSTRACT: Nucleobase building blocks have been demonstrated to be strong candidates when it comes to DNA/RNA-like materials by benefiting from hydrogen bond interactions as physical properties. Modifying at the 5' position is the simplest way to develop nucleobase-based structures by transesterification using the lipase Novozym 435. Herein, we describe the optimization of the lipase-catalyzed synthesis of the monomer 5'-O-methacryloylcytidine with the assistance of microwave irradiation. Variable reaction parameters, such as enzyme concentration, molar ratio of the substrate, reaction temperature and reaction time, were investigated to find the optimum reaction condition in terms of obtaining the highest yield.

SUBMITTER: Chea S

PROVIDER: S-EPMC9268227 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Glyceric Prodrug of Ursodeoxycholic Acid (UDCA): Novozym 435-Catalyzed Synthesis of UDCA-Monoglyceride.

Project description:Bile acids (BAs) are a family of steroids synthesized from cholesterol in the liver. Among bile acids, ursodeoxycholic acid (UDCA) is the drug of choice for treating primary biliary cirrhosis and dissolving cholesterol gallstones. The clinical effectiveness of UDCA includes its choleretic activity, the capability to inhibit hydrophobic bile acid absorption by the intestine under cholestatic conditions, reducing cholangiocyte injury, stimulation of impaired biliary output, and inhibition of hepatocyte apoptosis. Despite its clinical effectiveness, UDCA is poorly soluble in the gastro-duodeno-jejunal contents, and pharmacological doses of UDCA are not readily soluble in the stomach and intestine, resulting in incomplete absorption. Indeed, the solubility of 20 mg/L greatly limits the bioavailability of UDCA. Since the bioavailability of drug products plays a critical role in the design of oral administration dosages, we investigated the enzymatic esterification of UDCA as a strategy of hydrophilization. Therefore, we decided to enzymatically synthesize a glyceric ester of UDCA bile acid to produce a more water-soluble molecule. The esterification reactions between UDCA and glycerol were performed with an immobilized lipase B from Candida antarctica (Novozym 435) in solvent-free and solvent-assisted systems. The characterization of the UDCA-monoglyceride, enzymatically synthesized, has been performed by 1H-NMR, 13C-NMR, COSY, HSQC, HMBC, IR, and MS spectroscopy.

| S-EPMC8513054 | biostudies-literature

Novozym 435-Catalyzed Synthesis of Well-Defined Hyperbranched Aliphatic Poly(β-thioether ester).

Project description:A series of new hyperbranched aliphatic poly(β-thioether ester)s were prepared by the enzymatic ring-opening polycondensation of 1,4-oxathiepan-7-one (OTO) and AB2/ABB' comonomer with acid-labile β-thiopropionate groups. Two kinds of comonomers, methyl 3-((3-hydroxy-2-(hydroxymethyl)propyl)thio)propanoate (HHTP) and methyl 3-((2,3-dihydroxypropyl)thio)propanoate (DHTP), with different primary alcohols and secondary alcohols, were synthesized by thiol-ene click chemistry and thiol-ene Michael addition, respectively. Immobilized lipase B from Candida antarctica (CALB), Novozym 435, was used as the catalyst. The random copolymers were characterized by 1H-NMR, 13C-NMR, GPC, TGA, and DSC. All branched copolyesters had high molecular weights over 15,000 Da with narrow polydispersities in the range of 1.75-2.01 and were amorphous polymers. Their degradation properties under acidic conditions were also studied in vitro. The polymeric nanoparticles of hyperbranched poly(β-thioether ester)s were successfully obtained and showed good oxidation-responsive properties, indicating their potential for biomedical applications.

| S-EPMC7037349 | biostudies-literature

Highly efficient preparation of 1-lysophosphatidylcholine via high proportion of Novozym® 435 (lipase B from <i>Candida antarctica</i>)-catalyzed ethanolysis.

Project description:Efficient preparation methods for 1-lysophosphatidylcholine (1-LPC), a physiologically important compound, are lacking. Here, we established a method for 1-LPC preparation via Novozym® 435 (a lipase B from Candida antarctica)-catalyzed ethanolysis. Novozym® 435 showed sn-1 regiospecificity to phosphatidylcholine, although it does not exhibit regiospecificity to triacylglycerol. In particular, quantitative 1-LPC yields (96.5 ± 0.2 mol%) were reliably obtained in the presence of Novozym® 435 (100 wt% of PC), 97 % ethanol, in 72 h at 40 °C. During the reaction, acyl migration from 1-LPC to 2-LPC was rare. This novel synthetic method is expected to expand the practical applications of 1-LPC.

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Biocatalytic synthesis of vitamin A palmitate using immobilized lipase produced by recombinant Pichia pastoris.

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Alkali Niobate Powder Synthesis Using an Emerging Microwave-Assisted Hydrothermal Method.

Project description:For more than five decades, alkali niobate-based materials (KxNa1-xNbO3) have been one of the most promising lead-free piezoelectric materials researched to be used in electronics, photocatalysis, energy storage/conversion and medical applications, due to their important health and environmentally friendly nature. In this paper, our strategy was to synthetize the nearest reproductible composition to KxNa1-xNbO3 (KNN) with x = 0.5, placed at the limit of the morphotropic phase boundary (MPB) with the presence of both polymorphic phases, orthorhombic and tetragonal. The wet synthesis route was chosen to make the mix crystal powders, starting with the suspension preparation of Nb2O5 powder and KOH and NaOH alkaline solutions. Hydrothermal microwave-assisted maturation (HTMW), following the parameter variation T = 200-250 °C, p = 47-60 bar and dwelling time of 30-90 min, was performed. All powders therefore synthesized were entirely KxN1-xNbO3 solid solutions with x = 0.06-0.69, and the compositional, elemental, structural and morphological characterization highlighted polycrystalline particle assemblage with cubic and prismatic morphology, with sizes between 0.28 nm and 2.95 μm and polymorphic O-T phase coexistence, and a d33 piezoelectric constant under 1 pC/N of the compacted unsintered and unpoled discs were found.

| S-EPMC9369762 | biostudies-literature

Microwave-assisted synthesis of rhodamine derivatives.

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| S-EPMC7082095 | biostudies-literature

Microwave assisted synthesis of bridgehead alkenes.

Project description:A new, concise method to synthesize triene precursors for the type 2 intramolecular Diels-Alder reaction has been developed. Microwave irradiation of the trienes provides a convenient method for the synthesis of bridgehead alkenes. Higher yields, shorter reaction times, and lower reaction temperatures provide a general and efficient route to this interesting class of molecules.

| S-EPMC3064725 | biostudies-literature

Microwave-Assisted Synthesis of N-Phenylsuccinimide.

Project description:A microwave-assisted synthesis of N-phenylsuccinimide has been developed for the second-semester organic teaching laboratory. Utilizing this procedure, N-phenylsuccinimide can be synthesized by heating a mixture of aniline and succinic anhydride in a domestic microwave oven for four minutes in moderate yields (40-60%). This technique reduces the reaction time as compared to the traditional synthesis by several hours, which allows the preparation to be achieved in a single organic chemistry laboratory period. This reaction is performed in the absence of solvent, is energy efficient, and is atom economical; therefore, it represents a "greener" preparation than the traditional synthesis of N-phenylsuccinimide.

| S-EPMC3224042 | biostudies-literature

Enzymatic Synthesis of Glycerol Carbonate Using a Lipase Immobilized on Magnetic Organosilica Nanoflowers as a Catalyst.

Project description:For synthesizing glycerol carbonate (GC) by a reaction between glycerol (GL) and dimethyl carbonate (DMC), a lipase immobilized on magnetic organosilica nanoflowers was prepared and utilized as a biocatalyst. Candida antarctica lipase B (CALB) was chosen as a model enzyme for preparing an immobilized biocatalyst (CALB@nanoflowers). The obtained CALB@nanoflowers was characterized using scanning electron microscopy, transmission electron microscopy, and confocal laser scanning microscopy. Effects of GL/DMC molar ratio, biocatalyst amount, temperature, surfactant and molecular sieve addition, and reaction time on the conversion of GL and the selectivity of CALB@nanoflowers were investigated. The optimal catalytic performance (yield of GC: 88.66% and conversion of GL: 94.24%) was achieved under the condition of 1:20 molar ratio of GL to DMC with 0.2 g of molecular sieves added at 50 °C for 24 h. After recycling seven times, the CALB@nanoflowers maintained over 79% of its initial activity and the yield of GC was 70.31%.

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Synthesis of Hydroxyapatite with Antibacterial Properties Using a Microwave-Assisted Combustion Method.

Project description:The prevention of implant-associated infections has been increasing clinically in orthopedic surgery. Hydroxyapatite with antibacterial properties was synthesized using a microwave-assisted combustion method. High crystallinity at low temperature can be achieved using this method. The synthesized hydroxyapatite exhibited a superior clear zone for both Gram-positive and Gram-negative bacteria. Electron spin resonance (ESR) and X-ray photoelectron spectroscopy (XPS) were used for the radical investigation. The application of intelligent ink testing and an antioxidant assay using DPPH reduction were also used to confirm the existence of radicals. These techniques provided data confirming that radicals are responsible for the antibacterial properties. The synthesized antibacterial hydroxyapatite would be a good candidate for the prevention any infection with medical implants and injection materials causing failure in bone repair.

| S-EPMC6408465 | biostudies-literature

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