Bioconversion of substituted naphthalenes to the corresponding salicylic acids

Bestetti, Giovanna; Gennaro, Patrizia Di; Galli, E.; Leoni, Barbara; Pelizzoni, F.; Sello, Guido; Bianchi, D.

doi:10.1007/s002530050068

Cited by 2 publications

(3 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Among the various enzymes tested, the naphthalene dioxygenase employed in the present investigation is able to convert naphthalenes and other polycyclic aromatic hydrocarbons to the corresponding cis-dihydrodiols (Bestetti et al, 1994(Bestetti et al, , 1995Di Gennaro et al, 1997a, 1997b, 1997c. The limited solubilities of such substrates in water media (Table I) do not allow optimal turnover or production of large quantities of dihydroxylated products in a homogeneous phase.…”

Section: Resultsmentioning

confidence: 94%

“…The E. coli JM109 (pPS1778) recombinant strain carrying naphthalene dioxygenase and regulatory genes cloned from P. fluorescens N3 was used for bioconversion studies Di Gennaro et al, 1997a, 1997b. This biological system is able to catalyze the conversion of naphthalene and other polycyclic aromatic compounds to the corresponding cis,cis-dihydrodihydroxylated derivatives as previously reported (Bestetti et al, 1994(Bestetti et al, , 1995Di Gennaro et al, 1997a, 1997b, 1997c.…”

Section: Microorganismsmentioning

confidence: 99%

See 1 more Smart Citation

Efficient polycyclic aromatic hydrocarbons dihydroxylation in direct micellar systems

Randazzo

Berti

Briganti

et al. 2001

Biotech & Bioengineering

View full text Add to dashboard Cite

Optimization of whole-cell bioconversion of the polycyclic aromatic hydrocarbons (PAHs) anthracene, phenanthrene, and naphthalene to the enantiomerically pure corresponding cis-dihydroxydihydro derivatives by the Escherichia coli JM109 (pPS1778) recombinant strain, carrying the naphthalene dioxygenase and corresponding regulatory genes cloned from Pseudomonas fluorescens N3, in micellar systems, is presented. We show that direct microemulsion systems, where a nonionic surfactant such as 1.5% (v/v) Triton X-100 plus 0.6% to 1.0% (v/v) selected oils are able to solubilize the PAHs tested at relatively high concentrations (initial concentrations in the reaction medium > or =10 mM for naphthalene and phenanthrene and > or =2 mM for anthracene), and allow for more efficient substrate bioconversion. These media, while not affecting bacteria viability and performance, provide increased efficiency and final product yields (100% for naphthalene, >30% for anthracene, >60% for phenanthrene). The phase behavior of the direct microemulsion systems for the different substrates and oils utilized was monitored as a function of their volume fraction by light scattering experiments, and related to the bioconversion results. For anthracene and phenanthrene, the dihydroxylated products have an inhibitory effect on the conversion reactions, thus hindering complete turnover of the substrates. We ascertain that such inhibition is reversible because removal of the products formed allowed the process to start over at rates comparable to initial rates. To allow for complete conversion of the PAHs tested a stepwise or continuous separation of the product formed from the micellar reaction environment is being developed.

show abstract

Section: Resultsmentioning

confidence: 94%

Section: Microorganismsmentioning

confidence: 99%

Efficient polycyclic aromatic hydrocarbons dihydroxylation in direct micellar systems

Randazzo

Berti

Briganti

et al. 2001

Biotech & Bioengineering

View full text Add to dashboard Cite

show abstract

“…The 2,3-DMN was transformed to a single product of molecular weight 166. Comparison of these data to the results of a number of other studies [21][22][23] leads to the identification of this product as 4,5-dimethylsalicylic acid. No incorporation of a single hydroxyl group was observed in the transformation of 1,3-DMN and 2,3-DMN by strain 5RL.…”

Section: Biotransformation Of Methyl-substituted Naphthalenes By P Fmentioning

confidence: 63%

Structure–toxicity Assessment of Metabolites of the Aerobic Bacterial Transformation of Substituted Naphthalenes

Leblond¹,

Applegate²,

Menn³

et al. 2000

Environ Toxicol Chem

View full text Add to dashboard Cite

Pseudomonas fluorescens 5R, a naphthalene-degrading bacterium isolated from manufactured gas plant soil contaminated with polycyclic aromatic hydrocarbons, was examined for its degradative capacity of a number of substituted naphthalenes. In general, those compounds substituted on only one ring with an electrically neutral substituent were found to be transformed primarily to substituted salicylic acids according to the classical (NAH7) naphthalene dioxygenase-initiated upper pathway reactions of the naphthalene degradative pathway (i.e., the NAH system). Dimethylnaphthalenes with a substituent on each ring, and certain halogenated naphthalenes, were transformed via a monohydroxylation reaction to form hydroxylated dead-end products. Of the substituted salicylic acids examined, only 3-and 4-methylsalicylic acid, the respective products of the degradation of 1-and 2methylnaphthalene, were further degraded by salicylate hydroxylase and catechol 2,3-dioxygenase, the first two enzymes of the NAH lower pathway. Using the Tetrahymena pyriformis acute toxicity assay, many of the monohydroxylated products of incomplete biodegradation were found to be polar narcotics. Substituted salicylic acids that are not further degraded by the NAH lower pathway were found to be toxic via carboxylic acid narcosis.

show abstract

Bioconversion of substituted naphthalenes to the corresponding salicylic acids

Cited by 2 publications

References 0 publications

Efficient polycyclic aromatic hydrocarbons dihydroxylation in direct micellar systems

Efficient polycyclic aromatic hydrocarbons dihydroxylation in direct micellar systems

Structure–toxicity Assessment of Metabolites of the Aerobic Bacterial Transformation of Substituted Naphthalenes

Contact Info

Product

Resources

About