1123760-85-9Relevant academic research and scientific papers
Microbial oxidation of naphthalene derivatives. Absolute configuration of metabolites
Deluca,Hudlicky
, p. 13 - 16 (1990)
2-Methylnaphthalene was subjected to microbial oxidation by Pseudomonas putida 39D and Pseudomonas putida NCIB 9816 organisms. The structure and absolute stereochemistry of the major metabolite is reported and its use in enantioselective synthesis is indicated.
Toluene dioxygenase-catalyzed synthesis of cis-dihydrodiol metabolites from 2-substituted naphthalene substrates: Assignments of absolute configurations and conformations from circular dichroism and optical rotation measurements
Kwit, Marcin,Gawronski, Jacek,Boyd, Derek R.,Sharma, Narain D.,Kaik, Magdalena,More O'Ferrall, Rory A.,Kudavalli, Jaya S.
scheme or table, p. 11500 - 11511 (2009/12/03)
cis-Dihydrodiol metabolites have been isolated from naphthalene and six 2-substituted naphthalene substrates. Their structures and absolute configurations have been determined by a combination of calculated (TDDFT) and experimentally based circular dichroism (CD) and optical rotation (OR) methods. The inverse styrene helicity rule is shown to be incorrect for the interpretation of theCD spectra of cis-dihydrodiols. A striking conclusion is that CD spectra correlate directly with the helicity of the styrene chromophore: that is, the sign of the long-wavelength Cotton effect is identical with the sign of styrene torsion angle, whereas the OR sign is dependent on the absolute configuration of the allylic carbon atom. The results demonstrate that a predictive model previously used for the determination of preferred regio- and stereoselectivity associated with TDO-catalyzed cis-dihydroxylation of substituted benzene substrates can now be successfully extended to substituted naphthalene substrates.
