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Characterization of the biological conversion of naphthalene to (+)-cis-(1R,2S)-dihydroxy-1,2-dihydronaphthalene in direct micellar systems
Authors:Fabrizio Briganti  Demetrio Randazzo  Andrea Scozzafava  Debora Berti  Piero Baglioni  Patrizia Di Gennaro  Enrica Galli  Giuseppina Bestetti
Institution:

a Laboratorio di Chimica Inorganica e Bioinorganica, Dipartimento di Chimica, Università di Firenze, Via Gino Capponi 7, 50121, Florence, Italy

b Laboratorio di Chimica Fisica delle Interfasi, Dipartimento di Chimica, Università di Firenze, Via Gino Capponi 7, 50121, Florence, Italy

c Dipartimento di Genetica e Biologia dei Microorganismi, Università di Milano, Milan, Italy

Abstract:The whole cell biological conversion of naphthalene to (+)-cis-(1R,2S)-dihydroxy-1,2-dihydronaphthalene by the E. coli JM109(pPS1778) recombinant strain carrying the naphthalene dioxygenase and regulatory genes cloned from Pseudomonas fluorescens N3 in micellar systems has been investigated using biochemical and chemico-physical techniques. Reverse and direct micellar systems have been tested. Non-ionic surfactants (Tween and Triton X series) were found not to inhibit either the growth of the bacteria and the expression of the hydroxylating dioxygenase enzyme in such systems and were utilized in order to speed up the naphthalene conversion by increasing its solubility and also its bioavailability. The phase behavior of the direct micellar system was characterized through light scattering and other chemico-physical techniques. Further addition of isopropyl-palmitate 1–2% v/v to the micellar systems resulted in an increase of the apparent substrate concentration in solution and particularly its bioavailability thus allowing faster catalytic conversions resulting in an increase in productivity for the process. Since the cis-dihydrodiols are acquiring considerable potential as chiral pool synthons in asymmetric synthesis for a variety of industrial processes, possible applications for efficient small and large-scale production of such compounds are discussed.
Keywords:Naphthalene  (+)-cis-(1R  2S)-dihydroxy-1  2-dihydronaphthalene  Naphthalene dioxygenase  Compartmentalized biosystems  Direct micellar systems  E  coli JM109(pPS1778) recombinant strain  Pseudomonas fluorescens N3
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