Construction of an enzyme-targeted organophosphonate using immobilized enzyme and whole-cell synthesis

Reimer, L. M.; Conley, D. L.; Pompliano, David L.; Frost, J. W.

doi:10.1021/ja00285a022

Cited by 65 publications

(10 citation statements)

References 1 publication

(3 reference statements)

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“…In parallel, to further optimize the process and to improve storage, thermal and/or pH stability of the enzyme, immobilization on supports is of great interest . TK immobilization has been investigated on organic or semiorganic supports, such as activated sepharose, Eupergit‐C, Amberlite XAD‐7 and Nylon, and polyacrylamide gel . We have also reported the immobilization of TK yst and TK eco on an inorganic support, layered double hydroxides (LDHs).…”

Section: Introductionmentioning

confidence: 99%

“…[42,43] TK immobilization has been investigated on organic or semiorganic supports, such as activated sepharose, [44] Eupergit-C, Amberlite XAD-7 and Nylon, [45][46][47] and polyacrylamide gel. [48] We have also reported the immobilization of TK yst [49] and TK eco [50] on an inorganic support, layered double hydroxides (LDHs). LDHs are synthetic materials with positively charged brucite-like layers of mixed metal hydroxides that are described by the abbreviated formula [M 2+ + M 3+ + A],i nw hichM 2+ + and M 3+ + are divalent and trivalent metals, respectively,a nd Ai s the interlayer anion that compensates fort he positive charge of the metal layers.…”

Section: Introductionmentioning

confidence: 99%

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Chiral Polyol Synthesis Catalyzed by a Thermostable Transketolase Immobilized on Layered Double Hydroxides in Ionic liquids

et al. 2015

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In this work we set out to study the activity of a thermostable Transketolase (TK) from Geobacillus stearothermophilus (TKgst) in an ionic liquid as cosolvent, which has never been investigated before with this enzyme. 1‐Butyl‐3‐methylimidazolium chloride ([BMIm][Cl]) in the range 30–50 % in water maintained the total activity of TKgst and increased the reaction rate in the presence of pentoses as acceptor substrates, particularly d‐ribose. To improve the synthetic process, TKgst was immobilized on an inorganic support, layered double hydroxides (LDHs), with excellent immobilization yield and catalytic activity using a simple, eco‐compatible, efficient coprecipitation procedure. The biohybrid MgAl@TKgst was tested in 30 % [BMIm][Cl] for the synthesis of a rare, very costly commercially available sugar, d‐sedoheptulose, which was obtained in one step from d‐ribose with an isolated yield of 82 %. This biohybrid was reusable over four cycles with no loss of enzymatic activity. The particular activity of free and immobilized TKgst in [BMIm][Cl] holds promise to extend the applications of TKgst in other ionic liquids and unusual media in biocatalysis.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chiral Polyol Synthesis Catalyzed by a Thermostable Transketolase Immobilized on Layered Double Hydroxides in Ionic liquids

et al. 2015

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“…In order to improve synthetic processes based on TK‐catalyzed reactions, a handful of studies has described TK immobilization methods including covalent immobilization of the enzyme by BrCN activation of Sepharose29, on resin beads such as Eupergit‐C30, Amberlite XAD‐7,31 or nylon 32. More recently, variants of the wild‐type TK engineered with a his 6 ‐tag were reversibly immobilized via Ni‐NTA linkage to surface‐derivatized units in a fused‐silica capillary 33…”

Section: Introductionmentioning

confidence: 99%

Efficient Immobilization of Yeast Transketolase on Layered Double Hydroxides and Application for Ketose Synthesis

et al. 2011

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Transketolase (TK) from S. cerevisiae was successfully immobilized on layered double hydroxides (LDH) using simple, affordable and efficient adsorption and coprecipitation based immobilization procedures. Optimization of the preparation was performed using zinc aluminium nitrate (Zn 2 Al-NO 3 ) and magnesium aluminium nitrate (Mg 2 Al-NO 3 ) LDH as immobilization supports, and the protein-to-LDH weight ratio (Q) was varied. The highest immobilization yields (98-99%) and highest relative specific activities (4.2-4.4 U·mg À1 for the immobilized enzyme compared to 4.5 U·mg À1 for the free enzyme) were both achieved when using a proteinto-LDH weight ratio (Q) of 0.38. Efficient lyophilization of the LDH-TK bionanocomposites thus synthesized was proven to allow easy use and storage of the supported TK with no significant loss of activity over a three-month period. The kinetic parameters of the LDH-TK enzyme were comparable to those of the free TK. The LDH-TK enzyme was finally tested for the synthesis of l-erythrulose starting from hydroxypyruvate lithium salt (Li-HPA) and glycolaldehyde (GA) as substrates. l-erythrulose was characterized and obtained with an isolated yield of 56% similar to that obtained with free TK. The reusability of the LDH-TK biohybrid material was then investigated, and we found no loss of enzymatic activity over six cycles.

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“…1,3-Dithianes have been successfully used in reactions with (i) alkyl halides, sulfonates and triflates; [23][24][25][26][27][28] (ii) oxiranes 23,[29][30][31] and three-to six-membered cyclic ethers; 29 (iii) carbonyl compounds; 23,32,33 (iv) acid halides 34,35 and chloroformates; 29,36,37 (v) imines; 23 and (vi) electron deficient olefins [38][39][40] (Scheme 6). …”

Section: Methodsmentioning

confidence: 99%

Acyl anion synthons: benzotriazole stabilized compared to classical

Katritzky¹,

Kirichenko²

2006

Arkivoc

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Construction of an enzyme-targeted organophosphonate using immobilized enzyme and whole-cell synthesis

Cited by 65 publications

References 1 publication

Chiral Polyol Synthesis Catalyzed by a Thermostable Transketolase Immobilized on Layered Double Hydroxides in Ionic liquids

Chiral Polyol Synthesis Catalyzed by a Thermostable Transketolase Immobilized on Layered Double Hydroxides in Ionic liquids

Efficient Immobilization of Yeast Transketolase on Layered Double Hydroxides and Application for Ketose Synthesis

Acyl anion synthons: benzotriazole stabilized compared to classical

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