Cascade Catalysis Through Bifunctional Lipase Metal Biohybrids for the Synthesis of Enantioenriched O‐Heterocycles from Allenes

Naapuri, Janne M.; García, Noelia Losada; Rothemann, Robin Alexander; Pichardo, Manuel Carmona; Prechtl, Martin H. G.; Palomo, José M.; Deska, Jan

doi:10.1002/cctc.202200362

Cited by 12 publications

(11 citation statements)

References 53 publications

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“…However, the combination of both worlds must be employed in a reasonable way, taking advantage of both catalysis but also being aware of existing limitations to advance, and therefore considering solutions in the reaction setups. − There is no more powerful technique than organometallic chemistry for C–C or C–X bond formation, while enzymes can provide unique possibilities for chiral induction, so their cooperative work in one-pot multistep transformations undoubtedly constitutes one of the most straightforward manners to design controlled complexity. Gladly, this is an area in continuous evolution, and remarkable examples have recently appeared in the literature including valuable chemoenzymatic cascades. − …”

Section: Challenges Perspectives and Conclusionmentioning

confidence: 99%

Expanding the Synthetic Toolbox through Metal–Enzyme Cascade Reactions

et al. 2023

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The combination of metal-, photo-, enzyme-, and/or organocatalysis provides multiple synthetic solutions, especially when the creation of chiral centers is involved. Historically, enzymes and transition metal species have been exploited simultaneously through dynamic kinetic resolutions of racemates. However, more recently, linear cascades have appeared as elegant solutions for the preparation of valuable organic molecules combining multiple bioprocesses and metal-catalyzed transformations. Many advantages are derived from this symbiosis, although there are still bottlenecks to be addressed including the successful coexistence of both catalyst types, the need for compatible reaction media and mild conditions, or the minimization of cross-reactivities. Therefore, solutions are here also provided by means of catalyst coimmobilization, compartmentalization strategies, flow chemistry, etc. A comprehensive review is presented focusing on the period 2015 to early 2022, which has been divided into two main sections that comprise first the use of metals and enzymes as independent catalysts but working in an orchestral or sequential manner, and later their application as bionanohybrid materials through their coimmobilization in adequate supports. Each part has been classified into different subheadings, the first part based on the reaction catalyzed by the metal catalyst, while the development of nonasymmetric or stereoselective processes was considered for the bionanohybrid section.

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Section: Challenges Perspectives and Conclusionmentioning

confidence: 99%

Expanding the Synthetic Toolbox through Metal–Enzyme Cascade Reactions

et al. 2023

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“…A developed method for the production of lipophilic esters of hydroxytyrosol, which were synthesized from tyrosol and long-side chain carboxylic acids in a one-pot process by an enzymatic cascade of lipase M and tyrosinase supported by lignin nanoparticles [ 151 ]. Additionally, the synthesis of enantiomer-enriched O-heterocycles from alleles catalyzed by a cascade of bifunctional lipase metal bioheterozygotes was also achieved [ 152 ] ( Figure 10 ). Thus, it can be inferred that enzymes assembled by various methods have great application prospects in polymer synthesis.…”

Section: One-step Synthesis For Enzyme Assembliesmentioning

confidence: 99%

“… Synthesis of metal nano-biohybrids using enzyme–polymer conjugates. Illustrating the attempted prevention of mutual deactivation of the coupled enzyme and metal entities through poisoning effects in the nano-biohybrid synthesis by using polymer additives in the structure of the enzyme–metal nano-biohybrids [ 152 ], with permission from Wiley periodicals Inc., copyright (2022). …”

Section: Figurementioning

confidence: 99%

Advances in the One-Step Approach of Polymeric Materials Using Enzymatic Techniques

et al. 2023

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The formulation in which biochemical enzymes are administered in polymer science plays a key role in retaining their catalytic activity. The one-step synthesis of polymers with highly sequence-controlled enzymes is a strategy employed to provide enzymes with higher catalytic activity and thermostability in material sustainability. Enzyme-catalyzed chain growth polymerization reactions using activated monomers, protein–polymer complexation techniques, covalent and non-covalent interaction, and electrostatic interactions can provide means to develop formulations that maintain the stability of the enzyme during complex material processes. Multifarious applications of catalytic enzymes are usually attributed to their efficiency, pH, and temperature, thus, progressing with a critical structure-controlled synthesis of polymer materials. Due to the obvious economics of manufacturing and environmental sustainability, the green synthesis of enzyme-catalyzed materials has attracted significant interest. Several enzymes from microorganisms and plants via enzyme-mediated material synthesis have provided a viable alternative for the appropriate synthesis of polymers, effectively utilizing the one-step approach. This review analyzes more and deeper strategies and material technologies widely used in multi-enzyme cascade platforms for engineering polymer materials, as well as their potential industrial applications, to provide an update on current trends and gaps in the one-step synthesis of materials using catalytic enzymes.

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“…More recently, Janne et al constructed the lipase-Ag or lipase-Au hybrid catalysts by using enzyme-polyelectrolyte conjugate as the template. [15,16] The lipase is from Candida Antarctica (CALB). Two different polyelectrolytes, PEI with positive charge and dextran-aspartic acid polymer (Dext) with negative charge were used to form the enzyme-polyelectrolyte conjugate via electrostatic interaction (Figure 3).…”

Section: Polyelectrolytementioning

confidence: 99%

“…More recently, Janne et al. constructed the lipase‐Ag or lipase‐Au hybrid catalysts by using enzyme‐polyelectrolyte conjugate as the template [15,16] . The lipase is from Candida Antarctica (CALB).…”

Section: Enzyme‐polymer Conjugate As Nanoreactorsmentioning

confidence: 99%