New Biosilified Pd-lipase hybrid biocatalysts for dynamic resolution of amines

Souza, Stefânia P. de; Leão, Raquel A. C.; Bassut, Jonathan; Leal, Ivana Corrêa Ramos; Wang, Shuai; Ding, Qiqi; Li, Yingying; Lam, Frank Leung Yuk; Souza, Rodrigo O. M. A. de; Itabaiana, Ivaldo

doi:10.1016/j.tetlet.2017.11.031

Cited by 17 publications

(16 citation statements)

References 23 publications

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“…Platinum‐encapsulated zeolitic microcapsular catalyst has been used in the DKR of 1‐phenylethylamine . Recently, a palladium catalyst Glt‐Pd‐SiO 2 @APTES was used as a support for CAL‐B immobilization and this hybrid biocatalyst successfully catalyzed the DKR of α‐methylbenzylamine …”

Section: Introductionsupporting

confidence: 83%

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Racemization of Secondary‐Amine‐Containing Natural Products Using Heterogeneous Metal Catalysts

et al. 2018

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Heterogeneously catalyzed racemization reactions of the secondary amines (S)‐1‐methyl‐6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline (salsolidine) and (S)‐1‐methyl‐1,2,3,4‐tetrahydro‐ß‐carboline were investigated using Pd, Pt, and Ir on carbon or Al2O3 supports. A comparison of kinetics and deactivation on selected platinum and iridium catalysts was performed. Furthermore, the relative stabilities of (S)‐salsolidine and the corresponding imine on Pt(1 1 1) and Ir(1 1 1) surfaces were analyzed by density functional theory calculations. The racemization was faster on platinum and took place without detectable byproduct formation. Iridium, however, proved reusable and, in contrast to the platinum catalyst, deactivation at low catalyst concentration was not observed. Also, the physisorption of (S)‐salsolidine and the imine was stronger on platinum than on iridium.

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Section: Introductionsupporting

confidence: 83%

“…In contrast to the racemization of sec ‐alcohols, the development of efficient approaches for DKR and racemization of amines has remained challenging . Mechanistically, the racemization of amines typically involves dehydrogenation followed by re‐addition of hydrogen to the initially formed imine.…”

Section: Introductionmentioning

confidence: 99%

Racemization of Secondary‐Amine‐Containing Natural Products Using Heterogeneous Metal Catalysts

et al. 2018

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“…As a representative member of this MCHM family, we can mention the material recently synthesised by De Souza et al via the covalent immobilisation of CalB on functionalised silica with supported Pd nanoparticles. 29 This multi-catalytic material facilitated the dynamic kinetic resolution of α-methylbenzylamine, which usually involves the use of several catalysts in separate steps or at higher concentrations. At a Pd loading of 1 wt.%, the final enantiomeric excess exceeded 99 %, and conversion equalled 82 %, which resulted in increased productivity (2.21 vs. 0.76 mg.h −1 .mgcarrier −1 for Novozyme 435®, a common commercial lipase).…”

Section: Supports With a Rigid Structurementioning

confidence: 99%

Optimisation of catalysts coupling in multi-catalytic hybrid materials: perspectives for the next revolution in catalysis

et al. 2021

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“…The proximity of Pd NCs with Cal-A inside SiJAR, would stabilize a favorable transition state for high enantioselectivity. [20,23] In a test reaction, 4-nitrobenzaldehyde (0.1 mM) was reacted with acetone in the presence of Cal-Pd@SiJAR at r.t. for 30 h, affording the aldol product in quantitative yield (> 99 % by 1 H NMR) and good enantiomeric excess (ee = ca. 95 %) (Figure 4, S12-S14).…”

Section: Angewandte Chemiementioning

confidence: 99%

Silica Jar‐with‐Lid as Chemo‐Enzymatic Nano‐Compartment for Enantioselective Synthesis inside Living Cells

et al. 2021

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Nanodevices, harvesting the power of synthetic catalysts and enzymes to perform enantioselective synthesis inside cell, have never been reported. Here, we synthesized round bottom jar-like silica nanostructures (SiJARs) with a chemo-responsive metal-silicate lid. This was isolated as an intermediate structure during highly controlled solid-state nanocrystal-conversion at the arc-section of silica shell. Different catalytic noble metals (Pt, Pd, Ru) were selectively modified on the lid-section through galvanic reactions. And, lid aperture-opening was regulated by mild acidic conditions or intracellular environment which accommodated the metal nanocrystals and enzymes, and in turn created an openmouth nanoreactor. Distinct from the free enzymes, SiJARs performed asymmetric aldol reactions with high activity and enantioselectivity (yield > 99 %, ee = 95 %) and also functioned as the artificial catalytic organelles inside living cells. This work bridges the enormous potential of sophisticated nanocrystal-conversion chemistry and advanced platforms for new-to-nature catalysis.Evolutionary compartmentalization is the key structural feature of various organelles and cells to accommodate specific enzymes and cofactors, which effortlessly drive lifesustaining multistep biochemical cascades. [1] artificial organelle-like nanoreactors harnessing high activity of synthetic catalysts along with inherent handedness of enzymes, can result diversified platforms for bioorthogonal synthesis. [2, 3] These chemo-enzymatic systems can asymmetrically synthesize chiral enantiomeric bioactive molecules, [4] possessing distinct pharmacological and toxicological systemic responses and in turn leading to advanced bioimaging, therapeutic and biotechnological applications. [5] Variety of nature-inspired hollow nanostructures, which consist of silica/silicate [4b,c, 6] and polymers/micelles [3a, 7] confining catalytic nanocrystals (NCs), enzymes or both, have demonstrated improved catalysis that are mostly limited to abiotic conditions. [8] Microemulsion-, sacrificial template-, and one-pot entrapment-based methods for pre-encapsulation of bio/nano-catalysts inside a confining nano-housing, often involve difficult to control multiple synthetic steps, harsh conditions, biphasic non-aqueous solvents and complex reagents. [9] Major challenge to design nanoreactors for intracellular application is to reliably colocalize and maintain the reactive surfaces of catalytic NCs along with the protection of enzymes from de-activation. [4,10] In this regard, silica nanostructures are highly appealing for wide range of catalytic and biomedical applications owing to their chemical inertness, high stability, biocompatibility and synthetic flexibility. [11] Previously, we developed solid-state conversion strategy for reversible hollowing of silica-coated manganese oxide (MnO@SiO 2 ) [12] and the post-synthetic modification of the hollow silica interiors with catalytic noble metals. [13] However, these microporous closed shells restrict the entry and co-...

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New Biosilified Pd-lipase hybrid biocatalysts for dynamic resolution of amines

Cited by 17 publications

References 23 publications

Racemization of Secondary‐Amine‐Containing Natural Products Using Heterogeneous Metal Catalysts

Racemization of Secondary‐Amine‐Containing Natural Products Using Heterogeneous Metal Catalysts

Optimisation of catalysts coupling in multi-catalytic hybrid materials: perspectives for the next revolution in catalysis

Silica Jar‐with‐Lid as Chemo‐Enzymatic Nano‐Compartment for Enantioselective Synthesis inside Living Cells

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