Development of a multifunctional catalyst for a “relay” reaction

Ganai, Anal Kr.; Shinde, Pravin V.; Dhar, Basab Bijayi; Gupta, Sayam Sen; Prasad, B. L. V.

doi:10.1039/c2ra22829g

Cited by 25 publications

(21 citation statements)

References 39 publications

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“…Double-functionalized metallic nanoparticles with a core-shell structure were used to adsorb enzymes. Ganai et al 61 synthesized gold nanoparticles covered by mesoporous silica (Fig. 5c).…”

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Opportunities and challenges for combining chemo- and biocatalysis

et al. 2018

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N ature has evolved highly efficient systems in the form of cascade reactions, which assemble the metabolic networks that support life (growth and survival). The basic principle of cascade reactions is also frequently used in biocatalysis, using enzymes in isolation, as well as in combination with chemocatalysts (see Fig. 1 and Box 1 for definition of terms) [1][2][3][4][5][6][7] . As there is no need for purification and isolation of intermediates, operating time, production costs and waste are reduced, and concomitantly, overall yields are improved. In addition, the problem of unstable or difficult to handle intermediates can be overcome, and reactivity as well as selectivity can be enhanced by avoiding unfavourable reaction equilibria through the cooperative effects of multiple catalysts 8 . Starting in the 1980s, the early examples of the combination of chemo-and biocatalysts were reported by the van Bekkum group, who pioneered the development of a process to make the sugar substitute d-mannitol from readily available d-glucose through the combination of a heterogeneous metal-catalysed hydrogenation and an enzyme-catalysed isomerization 9 . The first broadly applied technology for the combination of enzyme and metalcatalysts, which was the research subject of many academic groups as well as industry, emerged in the 1990s from the Williams group 10,11 and aimed to achieve higher yields than classical kinetic resolution of racemates, thus overcoming the limitation of a maximum yield of 50% in the latter case. A prominent example of work that developed this theme is the combination of lipase-catalysed kinetic resolution via acylation of secondary alcohols with Pd-or Rh-catalysed racemization via reversible transfer hydrogenation to achieve a dynamic kinetic resolution (DKR) [12][13][14] . This example was facilitated in part because lipases are active and stable in organic solvents. Later, for instance, Turner's group combined a monoamine oxidase-catalysed imine formation with a chemical reduction 15 to achieve the 100% theoretical yield through a deracemization process. In addition to the combination of metalcatalysis with enzymes, organocatalysis, electrochemistry and light-induced reaction couples have since then been studied extensively, going far beyond the scope of a DKR.The challenges to combining chemo-and biocatalysis in cascades (see Box 1 for definitions and Table 1) can be daunting, not least the requirement for the chemical step to occur in the presence of water, the preferred solvent for enzymes 3 . This Review therefore highlights recent examples of the combination of chemo-and biocatalysts in aqueous multistep syntheses, and looks at how to overcome limitations by, for example, design of appropriate reaction conditions, protein engineering and advanced reactor concepts. Furthermore, trends such as the integration of transition metalcatalysis into microorganisms and the introduction of novel chemistry into engineered enzymes are discussed, and a critical assessment of the impact of this research ...

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“…Double-functionalized metallic nanoparticles with a core-shell structure were used to adsorb enzymes. Ganai et al 61 synthesized gold nanoparticles covered by mesoporous silica (Fig. 5c).…”

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confidence: 99%

“…The glucosidase hydrolysed 4-nitro-phenyl-β -glucopyranoside and the released 4-nitrophenol was immediately reduced to the corresponding amine by the gold nanoparticles in the presence of NaBH 4 (ref. 61 ). Unfortunately, recyclability of the catalytic particles was very low.…”

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Opportunities and challenges for combining chemo- and biocatalysis

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“…In addition, enzymes and metal nanopaticles can be positionally immobilized on a support with hierarchical structure, which can be utilized for the “relay” cascade reactions. One of these examples has been developed by Prasad and co‐workers, who prepared a cascade nanoreactor with core–shell architecture. In this work, Au nanoparticles were first encapsulated inside a mesoporous silica shell (Au@mSiO 2 ) by sol–gel procedure and glucosidase was subsequently grafted on the surface of the metal core –silica shell nanoparticle.…”

Section: Synthesis Of Enzyme–metal Hybrid Catalysts (Emhcs)mentioning

confidence: 99%

Enzyme–Metal Hybrid Catalysts for Chemoenzymatic Reactions

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et al. 2019

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“…Similarly,ametal-enzyme cascade reaction was realized where 4-nitrophenylglucopyranoside was hydrolyzed of by glucosidase in ac ompartment, and subsequently the 4nitrophenol produced was reduced in another compartment to 4-aminephenyl by the Au nanoparticle in the presence of NaBH 4 . [10] This tandem reaction was studied by UV/Vis spectroscopy,a ss hown in Figure 5b.T he gradual increase in the peak height at 400 nm with time indicates the formation of 4-nitrophenol (Figure 5b1). After the completion of the hydrolysis reaction, it was found that the peak at 400 nm disappeared within 5minutes in the presence of NaBH 4 , indicative of the reduction of 4-nitrophenol to 4-aminephenyl ( Figure 5b2).…”

Section: Angewandte Chemiementioning

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Efficient Construction of Well‐Defined Multicompartment Porous Systems in a Modular and Chemically Orthogonal Fashion

et al. 2017

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Am icrofluidic assembly approach was developed for efficiently producing hydrogel spheres with reactive multidomains that can be employed as an advantageous platform to create spherical porous networks in afacile manner with welldefined multicompartments and spatiotemporally controlled functions.T his strategy allows for not only large scale fabrication of various robust hydrogel microspheres with controlled size and porosity,but also the domains embedded in hydrogel network could be introduced in am odular manner. Additionally,t he number of different domains and their ratio could be widely variable on demand. More importantly,t he reactive groups distributed in individual domains could be used as anchor sites to further incorporate functional units in an orthogonal fashion, leading to well-defined multicompartment systems.The strategy provides anew and efficient route to construct well-defined functional multicompartment systems with great flexibility and extendibility.

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Development of a multifunctional catalyst for a “relay” reaction

Cited by 25 publications

References 39 publications

Opportunities and challenges for combining chemo- and biocatalysis

Opportunities and challenges for combining chemo- and biocatalysis

Enzyme–Metal Hybrid Catalysts for Chemoenzymatic Reactions

Efficient Construction of Well‐Defined Multicompartment Porous Systems in a Modular and Chemically Orthogonal Fashion

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