Asymmetric kinetic resolution polymerization

Xu, Guiying; Mahmood, Qaiser; Lv, Chengdong; Yang, Rong; Zhou, Li; Wang, Qinggang

doi:10.1016/j.ccr.2020.213296

Cited by 30 publications

(35 citation statements)

References 207 publications

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“…Up to now, a variety of metal complexes featuring elegant ligands have been widely developed, such as Co, Cr, Zn, Fe, and Al complexes, etc., which have been well summarized in many excellent reviews. [41][42][43][44][45][46][47] Compared with the metal catalyzed epoxide/CO 2 copolymerization process, organocatalysis can produce polycarbonates without the metal residue and attracts significant attention in more recent years. A major breakthrough of metal-free alternating epoxide/CO 2 copolymerization was reported by Gnanou and Feng in 2016 (Fig.…”

Section: Chemically Recyclable Polymers Derived From Three-membered R...mentioning

confidence: 99%

Chemically recyclable polymer materials: polymerization and depolymerization cycles

Wang

2022

Green Chem.

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Section: Chemically Recyclable Polymers Derived From Three-membered R...mentioning

confidence: 99%

Chemically recyclable polymer materials: polymerization and depolymerization cycles

Wang

2022

Green Chem.

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123

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“…Asymmetric epoxidation of unfunctionalized olefins represents an important organic transformation to prepare optically pure epoxides [96][97][98][99]; however, the (R)-enantioselective epoxidation of styrene seems more difficult to achieve than the (S)-enantioselective reaction through either synthetic molecular catalysts or natural enzymatic bio-catalysts [100][101][102][103][104][105][106][107][108]. DFSM-facilitated P450BM3 peroxygenase enabled access to (R)-enantioselective epoxidation of unfunctionalized styrene and its derivatives (Figure 5).…”

Section: Catalytic Applications Of the Dfsm-facilitated P450 Peroxyge...mentioning

confidence: 99%

A Unique P450 Peroxygenase System Facilitated by a Dual-Functional Small Molecule: Concept, Application, and Perspective

Fan

Jiang

et al. 2022

Antioxidants

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Cytochrome P450 monooxygenases (P450s) are promising versatile oxidative biocatalysts. However, the practical use of P450s in vitro is limited by their dependence on the co-enzyme NAD(P)H and the complex electron transport system. Using H2O2 simplifies the catalytic cycle of P450s; however, most P450s are inactive in the presence of H2O2. By mimicking the molecular structure and catalytic mechanism of natural peroxygenases and peroxidases, an artificial P450 peroxygenase system has been designed with the assistance of a dual-functional small molecule (DFSM). DFSMs, such as N-(ω-imidazolyl fatty acyl)-l-amino acids, use an acyl amino acid as an anchoring group to bind the enzyme, and the imidazolyl group at the other end functions as a general acid-base catalyst in the activation of H2O2. In combination with protein engineering, the DFSM-facilitated P450 peroxygenase system has been used in various oxidation reactions of non-native substrates, such as alkene epoxidation, thioanisole sulfoxidation, and alkanes and aromatic hydroxylation, which showed unique activities and selectivity. Moreover, the DFSM-facilitated P450 peroxygenase system can switch to the peroxidase mode by mechanism-guided protein engineering. In this short review, the design, mechanism, evolution, application, and perspective of these novel non-natural P450 peroxygenases for the oxidation of non-native substrates are discussed.

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“…Direct polymerization of enantioenriched monomers and asymmetric kinetic resolution polymerization (AKRP) of racemic monomers are two commonly used methods for constructing chiral polymers. [14][15][16][17][18][19][20][21][22] However, neither of them could efficiently afford chiral poly-triazolyl-methanamines due to the above-mentioned issues.…”

Section: Introductionmentioning

confidence: 99%

Three-Component Asymmetric Polymerization toward Chiral Polymer

Li¹,

Zheng

Duan

et al. 2022

CCS Chem

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Chiral-polymers with metal-coordination ability show great potentials in mediating asymmetric reactions. It still remains great challenge for the synthesis of structural diverse chiral polymers, especially in an efficient manner. Herein, four types of Cu-catalyzed multicomponent asymmetric polymerization were developed to facilely afford 30 chiral poly-triazolyl-methanamines with desired molecular weights (M n up to 46700 g/mol) and well-defined chiral structures using a flexible combination of OBoc-alkyne, amine and azide. As excellent ligands for coppers, such polytriazolyl-methanamines revealed unique catalytic performances. (1) Amphiphilic poly-triazolylmethanamines prepared from water-soluble azides could self-assemble into nanoparticles in water, exhibiting excellent catalytic efficiency for aqueous click reaction at a low Cu loading of 10 ppm. (2) Poly-triazolyl-methanamines obtained from aromatic amines owned the capability to enduringly stabilize cuprous upon the exposure to water and air for up to 42 days. (3) Chiral polytriazolyl-methanamines also outperformed commercial available chiral ligands, such as Py-box, in mediating asymmetric propargylic substitution reaction.

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Asymmetric kinetic resolution polymerization

Cited by 30 publications

References 207 publications

Chemically recyclable polymer materials: polymerization and depolymerization cycles

Chemically recyclable polymer materials: polymerization and depolymerization cycles

A Unique P450 Peroxygenase System Facilitated by a Dual-Functional Small Molecule: Concept, Application, and Perspective

Three-Component Asymmetric Polymerization toward Chiral Polymer

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