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Enzymatic carbon−carbon bond formation in water-in-oil highly concentrated emulsions (gel emulsions)

AuthorsEspelt, Laia; Clapés Saborit, Pere ; Esquena, Jordi ; Manich, Albert M. ; Solans, Conxita
KeywordsWater-in-oil (W/O)
Gel emulsions
Dihydroxyacetone phosphate (DHAP)
Issue Date25-Jan-2003
PublisherAmerican Chemical Society
CitationLangmuir 19(4): 1337–1346 (2003)
AbstractWater-in-oil (W/O) highly concentrated emulsions (gel emulsions) of water/C14E4/aliphatic hydrocarbon systems were investigated as reaction media for the aldolic condensation of dihydroxyacetone phosphate (DHAP) with acceptor aldehydes such as phenylacetaldehyde (1) and benzyloxyacetaldehyde (2), catalyzed by d-fructose-1,6-bisphosphate aldolase from rabbit muscle (RAMA). Prior to any enzymatic reaction, both the formation and stability of the W/O gel emulsions in the presence of reactants were assessed. It was found that the aldehydes improved greatly the kinetic stability of W/O gel emulsions at 25 °C by decreasing the hydrophile−lipophile balance temperature (THLB) of the water/C14E4/aliphatic hydrocarbon systems. Interestingly, the stability of RAMA in W/O gel emulsions was improved by 7- and 25-fold compared to that in aqueous medium or conventional dimethylformamide/water 1/4 v/v mixture, respectively. It was found that the equilibrium yields and enzymatic activity depended on both the aldehyde partitioning between the continuous and dispersed phases and the water−oil interfacial tension. The highest enzymatic activities were achieved in W/O gel emulsion systems with the lowest water−oil interfacial tension. The equilibrium yield depended on the water−oil interfacial tension for the hydrophobic phenylacetaldehyde, and on the partition coefficient for the hydrophilic benzyloxyacetaldehyde. Optimum equilibrium product yields (65−70%) were achieved at either the lowest water−oil interfacial tension or partition coefficient values.
Description10 pages, 11 figures, 1 scheme, 4 tables.-- Printed version published Feb 18, 2003.
Publisher version (URL)http://dx.doi.org/10.1021/la020811b
Appears in Collections:(IQAC) Artículos
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