Abstract
A new biotechnological synthetic approach to 4-hydroxybenzoic acid is reported. Thauera aromatica cells produce the phenylphosphate carboxylase enzyme that selectively carboxylates phenylphosphate in the para position, without any formation of the ortho isomer. Here we show that the enzyme also works in supercritical carbon dioxide, opening a new technological solution to the recovery of the products that is a key problem when aqueous media are used. The enzyme shows an activity comparable with that shown under CO2 pressure in aqueous media and does not require the presence of NaHCO3.
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References
Aresta M, Dibenedetto A (2002) Development of environmentally friendly syntheses: Use of enzymes and biomimetic systems for the direct carboxylation of organic substrates. Rev Mol Biotech 90:113–128
Aresta M, Quaranta E, Liberio R, Dileo C, Tommasi I (1998) Enzymatic synthesis of 4-OH-benzoic acid from phenol and CO2: The first example of a biotechnological application of a carboxylase enzyme. Tetrahedron 54:8841–8846
Lack A, Fuchs G (1992) Carboxylation of phenylphosphate by phenol carboxylase, an enzyme system of anaerobic phenol metabolism. J Bacteriol 174:3629–3636
Lack A, Tommasi I, Aresta M, Fuchs G (1991) Catalytic properties of phenol carboxylase. In vitro study of CO2: 4-Hydroxybenzoate isotope exchange reaction. Eur J Biochem 19:473–479
Matsuda T, Watanabe K, Harada T, Nakamura K (2004) Enzymatic reactions in supercritical CO2: Carboxylation, asymmetric reduction and esterification. Catal Today 96:103–111
Schuhle K, Fuchs G (2004) Phenyl phosphate carboxylase: A new C–C lyase involved in anaerobic phenol metabolism in Thauera aromatica. J Bacteriol 186(14):4556–4557
Waddell WJ, Chapel H (1956) A simple ultraviolet spectrophotometric method for the determination of protein. J Lab Clin Med 48(2):311–314
Wieser M, Yoshida T, Nagasawa T (1998) Microbial synthesis of pyrrole-2-carboxylate by Bacillus megaterium PYR 2910. Tetrahedron Lett 39:4309–4310
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We thank MIUR-PRIN 2003039774 for the financial support
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Dibenedetto, A., Lo Noce, R., Pastore, C. et al. First in vitro use of the phenylphosphate carboxylase enzyme in supercritical CO2 for the selective carboxylation of phenol to 4-hydroxybenzoic acid. Environ Chem Lett 3, 145–148 (2006). https://doi.org/10.1007/s10311-005-0019-9
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DOI: https://doi.org/10.1007/s10311-005-0019-9