Two Enzyme Cooperatively Catalyzed Tandem Polymerization for the Synthesis of Polyester Containing Chiral (<i>R</i>)‐ or (<i>S</i>)‐Ibuprofen Pendants

Qian, Xiaofei; Wang, Jianfeng; Li, Yanyan; Lin, Xianfu; Wu, Qi

doi:10.1002/marc.201400394

Cited by 9 publications

(7 citation statements)

References 47 publications

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“…Lipase CA-catalyzed polymerization of ε-CL in the presence of the first generation dendrimer gave the poly(ε-CL)-monosubstituted dendrimer . Ibuprofen, an important chiral 2-arylpropionic acid class of nonsteroidal anti-inflammatory drug, initiated lipase CA-catalyzed ROP of ε-CL, followed by polycondensation using alkaline protease from Bacillus subtilis to produce biodegradable polyesters with the drug pendants …”

Section: Hydrolasesmentioning

confidence: 99%

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Enzymes as Green Catalysts for Precision Macromolecular Synthesis

et al. 2016

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The present article comprehensively reviews the macromolecular synthesis using enzymes as catalysts. Among the six main classes of enzymes, the three classes, oxidoreductases, transferases, and hydrolases, have been employed as catalysts for the in vitro macromolecular synthesis and modification reactions. Appropriate design of reaction including monomer and enzyme catalyst produces macromolecules with precisely controlled structure, similarly as in vivo enzymatic reactions. The reaction controls the product structure with respect to substrate selectivity, chemo-selectivity, regio-selectivity, stereoselectivity, and choro-selectivity. Oxidoreductases catalyze various oxidation polymerizations of aromatic compounds as well as vinyl polymerizations. Transferases are effective catalysts for producing polysaccharide having a variety of structure and polyesters. Hydrolases catalyzing the bond-cleaving of macromolecules in vivo, catalyze the reverse reaction for bond forming in vitro to give various polysaccharides and functionalized polyesters. The enzymatic polymerizations allowed the first in vitro synthesis of natural polysaccharides having complicated structures like cellulose, amylose, xylan, chitin, hyaluronan, and chondroitin. These polymerizations are "green" with several respects; nontoxicity of enzyme, high catalyst efficiency, selective reactions under mild conditions using green solvents and renewable starting materials, and producing minimal byproducts. Thus, the enzymatic polymerization is desirable for the environment and contributes to "green polymer chemistry" for maintaining sustainable society.

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Section: Hydrolasesmentioning

confidence: 99%

“…On the basis of the enzymatic cooperative tandem polymerization, valuable chiral ( R )- or ( S )-ibuprofen-containing polyesters were tailor-made in high yields and ee values. The in vitro drug release behavior and degradation of the prepared chiral polymeric prodrug were also investigated …”

Section: Hydrolasesmentioning

confidence: 99%

Enzymes as Green Catalysts for Precision Macromolecular Synthesis

et al. 2016

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“…Enzymatic polymerization, which is beneficial for high efficiency, good biocompatibility, and environmental acceptability along with high stereopreference and chemoselectivity, has been increasingly applied in the synthesis of polyesters, polysaccharides, and polyamides. − Since Brenner and co-workers reported the first oligomerization of threonine and methionine esters catalyzed by α-chymotrypsin in 1950, more and more studies about enzymatic polymerization of amino acid ester have been reported by Gross, Numata, and other researchers starting from different amino acid esters. − Most of these works used protease in aqueous environment as the catalysis system, and oligomers were usually prepared. Among them, enzymatic polymerization method of aspartic acid was rarely reported due to its restriction only to oligomer formation, until Matsumura and co-workers’ report in 1999 .…”

Section: Introductionmentioning

confidence: 99%

Solvent-Free Lipase-Catalyzed Synthesis: Unique Properties of Enantiopured- andl- Polyaspartates and Their Complexation

Xia

Wang

et al. 2015

Biomacromolecules

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Amino acids are attractive monomers for the large-scale preparation of chiral polyamides. For enzymatic polymerization of amino acids using protease in aqueous environment as the catalysis system, one main restriction is oligomer formation, usually along with other displayed advantages. Herein we developed an efficient solvent-free lipase-catalyzed polymerization of diethyl D- or L-aspartate, providing chiral D- and L-polyaspartates with an average degree of polymerization (DPavg) up to 60 and having about 96% β-linkages. Additionally, their distinct chemical and physical properties were characterized by circular dichroism (CD) spectra, X-ray powder diffraction (XRD), microscopic observation, and thermal analysis. Poly(β-D-AspEt) and Poly(β-L-AspEt) showed vertically mirrored negative and positive CD signals, high crystallinity, and entirely different microscopic morphology. They are thermal stable while having different decomposition (Td), melting (Tm), and cold crystallization temperatures (Tcc), respectively. Our results also showed that the complexation of enantiopure D- and L-polyaspartates was not stereocomplex but homocomplex.

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“…[ 145 ] They used the cooperation between CALB and alkaline protease from Bacillus subtilis (BSP) in the copolymerization of bulky ibuprofen‐containing hydroxyacid methyl ester (HAEP) and ε ‐CL to improve molecular weight of the polymers. [ 147 ] This group also used the chemo‐enzymatic pathway to synthesize chiral polyesters from customize (R)‐ and (S)‐lactones, such as ω ‐substituted‐ δ ‐valerolactone [ 148 ] or 4‐substituted‐ ε ‐CL. [ 149 ] More recently, they applied the substrate engineering strategy, i.e., modifying d ‐aspartic acid diester structure to hide the chiral centers and, thus chiral polyesters of d ‐aspartic acid with M n up to 39 500 g mol −1 were successfully prepared.…”

Section: Polyesters Synthesized By Enzymatic Polymerizationmentioning

confidence: 99%

Enzymatic Synthesis of Polyesters and Their Bioapplications: Recent Advances and Perspectives

Hevilla

Sonseca

Echeverría

et al. 2021

Macromolecular Bioscience

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This article reviews the most important advances in the enzymatic synthesis of polyesters. In first place, the different processes of polyester enzymatic synthesis, i.e., polycondensation, ring opening, and chemoenzymatic polymerizations, and the key parameters affecting these reactions, such as enzyme, concentration, solvent, or temperature, are analyzed. Then, the latest articles on the preparation of polyesters either by direct synthesis or via modification are commented. Finally, the main bioapplications of enzymatically obtained polyesters, i.e., antimicrobial, drug delivery, or tissue engineering, are described. It is intended to point out the great advantages that enzymatic polymerization present to obtain polymers and the disadvantages found to develop applied materials.

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Two Enzyme Cooperatively Catalyzed Tandem Polymerization for the Synthesis of Polyester Containing Chiral (R)‐ or (S)‐Ibuprofen Pendants

Cited by 9 publications

References 47 publications

Enzymes as Green Catalysts for Precision Macromolecular Synthesis

Enzymes as Green Catalysts for Precision Macromolecular Synthesis

Solvent-Free Lipase-Catalyzed Synthesis: Unique Properties of Enantiopured- andl- Polyaspartates and Their Complexation

Enzymatic Synthesis of Polyesters and Their Bioapplications: Recent Advances and Perspectives

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