Metallomicelles as potent catalysts for the ester hydrolysis reactions in water

Bhattacharya, Santanu; Kumari, Namita

doi:10.1016/j.ccr.2009.01.016

Cited by 77 publications

(47 citation statements)

References 116 publications

(99 reference statements)

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“…The application of those compounds in polar media, ultimately water, requires extra effort. Here, we recommend the review published by Bhattacharya in 2009 . However, a remaining challenge is the compatibility of the catalytically active species with two solvents of opposing miscibility at the same time.…”

Section: Catalytic Surfactantsmentioning

confidence: 99%

Added‐Value Surfactants

Polarz

Kunkel

Donner

et al. 2018

Chemistry A European J

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Surfactants are ubiquitous in cellular membranes, detergents or as emulsification agents. Due to their amphiphilic properties, they cannot only mediate between two domains of very different solvent compatibility like water and organic but also show fascinating self-assembly features resulting in micelles, vesicles, or lyotropic liquid crystals. The current review article highlights some approaches towards the next generation surfactants, for example, those with catalytically active heads. Furthermore, it is shown that amphiphilic properties can be obtained beyond the classical hydrophobic-hydrophilic interplay, for instance with surfactants containing one molecular block with a special shape. Whereas, classical surfactants are static, researchers have become more interested in species that are able to change their properties depending on external triggers. The article discusses examples for surfactants sensitive to chemical (e.g., pH value) or physical triggers (temperature, electric and magnetic fields).

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Section: Catalytic Surfactantsmentioning

confidence: 99%

Added‐Value Surfactants

Polarz

Kunkel

Donner

et al. 2018

Chemistry A European J

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“…Endo-b-1,4-glucanase hydrolyzes internal glycosidic bonds in cellulose with a random, on-off fashion [24,25]. And the catalytic mechanism of endo-b-1,4-glucanase was believed to consist of two reaction steps involving glycosylation and deglycosylation steps [26,27].…”

Section: Introductionmentioning

confidence: 99%

Effective Cleavage of β-1,4-Glycosidic Bond by Functional Micelle with l-Histidine Residue

Liao¹,

Liu

Xiao³

et al. 2016

Catal Lett

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A novel functional surfactant N a -dodecyl-Lhistidine (NDH) was synthesized and its micelle was used as mimic of b-1,4-endoglucanase to catalyzed the hydrolysis of methyl-b-D-cellobioside (MCB) under relatively low temperatures (80-110°C). The results showed that the micelle of NDH displayed excellent catalytic activity for the cleavage of b-1,4-glycosidic bond and the formation ofThe micelle-catalyzed first-order reaction rate constant k m of degradation of MCB was calculated. The conversion of MCB and selectivity of reducing sugars (glucose and fructose) could reach 58.9 and 87.1 %, respectively, for a reaction time of 10 h at pH 4.0 and 110°C. In NDH micelle-catalyzed reaction sugar ester was deduced as the chief product. The reaction pathways of MCB hydrolysis were proposed and the activation energy Ea for the hydrolysis was calculated. Graphical AbstractO OCR OH OH HO HO pH4.0, 90 o C Selectivity>97% O O OH OH HO HO O OH OH OCH 3 HO Glucose Fructose + p H 1 2 . 0 , 2 5 o C O N N H NH HOOC C 12 H 25

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“…It is well accepted that the efficiency of metal ions in catalyzing hydrolytic phosphate transfers generally stems from the following major factors: (1) enhancement of substrate electrophilicity by coordination of the metal ion to basic heteroatoms adjacent to the electrophilic center, (2) nucleophilic enhancement of metallo‐bound water/hydroxide molecules, (3) stabilization by the metal ion of developing negative charges in the transition states and/or intermediates, and last, but not least, (4) assistance to leaving group departure …”

Section: Introductionmentioning

confidence: 99%

Cu(II)‐catalyzed hydrolysis of tris‐2‐pyridyl phosphate assisted by sodium dodecyl sulfate micelles

Wanderlind

Bittencourt

Manfredi

et al. 2018

J of Physical Organic Chem

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Hydrolysis of the phosphate triester tris‐2‐pyridyl phosphate is catalyzed upon complexation with Cu2+, with enhancements of the order of 107‐fold in comparison to the spontaneous hydrolysis of the substrate. Experimental and theoretical results suggest that Cu2+ most probably coordinates to the nitrogen atoms of two of the pyridyl substituents disposing a metallo‐bound water or hydroxo ligand at appropriate distance for intramolecular attack on phosphorus. Micelles of the anionic sodium dodecyl sulfate remarkably accelerate the reactions, acting as nanoreactors that concentrate in the micellar microenvironment both the hydrophobic substrate and the positively charged metal ion, favoring complexation between tris‐2‐pyridyl phosphate and Cu2+.

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Metallomicelles as potent catalysts for the ester hydrolysis reactions in water

Cited by 77 publications

References 116 publications

Added‐Value Surfactants

Added‐Value Surfactants

Effective Cleavage of β-1,4-Glycosidic Bond by Functional Micelle with l-Histidine Residue

Cu(II)‐catalyzed hydrolysis of tris‐2‐pyridyl phosphate assisted by sodium dodecyl sulfate micelles

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