ORGN 135 |
| We, and collaborating laboratories, have shown that polycyclic aromatic hydrocarbons (PAHs), e.g. anthracene, phenanthrene, chrysene, are metabolised by dioxygenases to yield enantiopure mono-cis-dihydrodiols. A new class of metabolite (bis-cis-dihydrodiols) containing four chiral centres, due to tetrahydroxylation on one face, was isolated from chrysene. Our objective was to find further evidence of this enzyme-catalysed tetraoxygenation process to yield other PAH members of this new class e.g. anthracene and phenanthrene. Further objectives include improving the stability and yield of both bis-cis-diols by formation of cis-tetrahydrodiol and acetonide derivatives of the first generation cis-dihydrodiol metabolites as substrates for a mutant strain of Sphingomonas yanoikuyae containing biphenyl dioxygenase. The isolation of bis-cis-diols from anthracene and phenanthrene has been achieved using enantiopure cis-diol substrates. The yield and stability of the bis-cis-dihydrodiols has been improved upon by the use of tetrahydrodiol and acetonide substrates. The structure and absolute configurations of these new metabolites have been determined. |
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Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster
Division of Organic Chemistry |