Download Tipo de Comunicación: Comunicación Oral Simposio: INGENIERÍA

Tipo de Comunicación:
Comunicación Oral
Simposio:
INGENIERÍA BIOQUÍMICA: BIOCATÁLISIS, BIORREACTORES, DOWNSTREAM,
BIOSENSORES E INTEGRACIÓN DE PROCESOS
Título:
Multienzyme oxidation of amino alcohols and aldol addition: reactions scheme for
chloroperoxidase and aldolase.
Autores:
Masdeu G., Valencia D., Guillén M., Caminal G., López-Santín J., Álvaro G.
Centro de Trabajo:
Departament d"Enginyeria Química, Biològica i Ambiental. Universitat Autònoma de
Barcelona.
Email:
[email protected]
Palabras Clave:
chloroperoxidase; aldolase; multienzyme reactions; amino alcohol oxidation; N-Cbz-3aminopropanol;
Comunicación:
Chloroperoxidase (CPO)-catalyzed oxidation of β-amino alcohols to yield β-amino
aldehydes is presented. Amino aldehydes have a special interest as substrates of aldolases
for stereoselective aldol addition of dihydroxyacetone (DHA) or dihydroxyacetone
phosphate (DHAP) to yield amino polyols, precursors of valuable imino cyclitols. This multienzymatic process requires coupling both enzymatic reactions in an efficient way,
minimizing secondary reactions and ensuring enzyme stability.
The above enzymatic oxidation requires peroxide, which concentration influences both the
oxidation rate as well as the enzymes activity. One-pot coupling with aldol addition using
DHAP or DHA dependent aldolases is expected to minimize further oxidation of amino
aldehydes to amino acid driving the reaction to the target products.
In the present research, the following aspects have been studied:
- Determination of the main operational conditions for the enzymatic oxidation: reaction
medium, substrate concentration and selection of peroxide.
- Identification of by-products in CPO oxidation of N-Cbz-β-aminopropanol employing H2O2
or tert-butyl hydroperoxide.
- Coupling of the enzymatic oxidation to aldol addition of DHA or DHAP using fructose-6phosphate aldolase (FSA) and rhamnulose-1-phosphate aldolase (RhuA) respectively.
Proposal of a reactions scheme including all secondary reactions.
- Stability of CPO and aldolases and enzymes immobilization.
The reported results constitute a necessary knowledge to determine the optimal conditions
for maximal product yield and to evaluate viability of the multi-enzymatic process.