Resolution and absolute configuration of K-region trans dihydrodiols from polycyclic aromatic hydrocarbons

Balani, Suresh K.; Bladeren, P.J. van; Shirai, Naohiro; Jerina, D. M.

doi:10.1021/jo00360a024

Cited by 28 publications

(23 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As noted previously by Jerina [19,29] and Armstrong, [22] it is just the sign of the shortwavelength B-band Cotton effects of 9,10-dihydrophenanthrenes that correctly reports the helicity of the biaryl chromophore ( Figure 3). As noted previously by Jerina [19,29] and Armstrong, [22] it is just the sign of the shortwavelength B-band Cotton effects of 9,10-dihydrophenanthrenes that correctly reports the helicity of the biaryl chromophore ( Figure 3).…”

Section: Resultssupporting

confidence: 76%

See 1 more Smart Citation

Circular Dichroism of 9,10-Dihydrophenanthrene Derivatives Reveals both the Absolute Configuration and Conformation: A Novel Approach to Mislow's Helicity Rule

et al. 2002

View full text Add to dashboard Cite

show abstract

Section: Resultssupporting

confidence: 76%

“…[29] Their results fit into the model of optical activity of 9,10-dihydrophenanthrene presented here. [29] Their results fit into the model of optical activity of 9,10-dihydrophenanthrene presented here.…”

Section: Resultssupporting

confidence: 57%

Circular Dichroism of 9,10-Dihydrophenanthrene Derivatives Reveals both the Absolute Configuration and Conformation: A Novel Approach to Mislow's Helicity Rule

et al. 2002

View full text Add to dashboard Cite

show abstract

“…CD spectra were expressed as ellipticity for methanol solutions that read 1.0 absorbance at 264 nm in a UV-visible spectrophotometer with a quartz cell of 1-cm path length. They were compared with published spectra (Miura et al 1968;Balani et al 1986) to determine the absolute configuration of the enantiomers.…”

Section: Circular Dichroismmentioning

confidence: 99%

Stereoselective formation of a K-region dihydrodiol from phenanthrene by Streptomyces flavovirens

et al. 1990

View full text Add to dashboard Cite

The metabolism of phenanthrene, a polycyclic aromatic hydrocarbon (PAH), by Streptomyces flavovirens was investigated. When grown for 72 h in tryptone yeast extract broth saturated with phenanthrene, the actinomycete oxidized 21.3% of the hydrocarbon at the K-region to form trans-9,10-dihydroxy-9,10-dihydrophenanthrene (phenanthrene trans-9,10-dihydrodiol). A trace of 9-phenanthrol was also detected. Metabolites isolated by thin-layer and high performance liquid chromatography were identified by comparing chromatographic, mass spectral, and nuclear magnetic resonance properties with those of authentic compounds. Experiments using [9-14C]phenanthrene showed that the trans-9,10-dihydrodiol had 62.8% of the radioactivity found in the metabolites. Circular dichroism spectra of the phenanthrene trans-9,10-dihydrodiol indicated that the absolute configuration of the predominant enantiomer was (-)-9S,10S, the same as that of the principal enantiomer produced by mammalian enzymes. Incubation of S. flavovirens with phenanthrene is an atmosphere of 18O2, followed by gas chromatographic/mass spectral analysis of the metabolites, indicated that one atom from molecular oxygen was incorporated into each molecule of the phenanthrene trans-9,10-dihydrodiol. Cytochrome P-450 was detected in 105,000 x g supernatants prepared from cell extracts of S. flavovirens. The results show that the oxidation of phenanthrene by S. flavovirens was both regio- and stereospecific.

show abstract

“…CD spectra of the phenanthrene trans-dihydrodiols were obtained in methanol with a Jasco model 500A spectropolarimeter (26) and were expressed as ellipticity (Iv) in millidegrees as described previously (14). Absolute configurations and optical purities were determined by comparing the molar ellipticities of the CD spectra (14) with those of phenanthrene trans-dihydrodiols of known absolute configuration (2,11,20).…”

mentioning

confidence: 99%

Enantiomeric Composition of the trans -Dihydrodiols Produced from Phenanthrene by Fungi

Sutherland

Yang

et al. 1993

Appl Environ Microbiol

View full text Add to dashboard Cite

The trans-dihydrodiols produced during the metabolism of phenanthrene by CunninghameUa elegans, Syncephalastrum racemosum, and Phanerochaete chrysosporium were purified by high-performance liquid chromatography (HPLC). The enantiomeric compositions and optical purities of the trans-dihydrodiols were determined to compare interspecific differences in the regio-and stereoselectivity of the fungal enzymes. Circular dichroism spectra of the trans-dihydrodiols were obtained, and the enantiomeric composition of each preparation was analyzed by HPLC with a chiral stationary-phase column. The phenanthrene trans-1,2dihydrodiol produced by C. elegans was a mixture of the 1R,2R and IS,2S enantiomers in variable proportions. The phenanthrene trans-3,4-dihydrodiol produced by P. chrysosporium was the optically pure 3R,4R

show abstract

Resolution and absolute configuration of K-region trans dihydrodiols from polycyclic aromatic hydrocarbons

Cited by 28 publications

References 1 publication

Circular Dichroism of 9,10-Dihydrophenanthrene Derivatives Reveals both the Absolute Configuration and Conformation: A Novel Approach to Mislow's Helicity Rule

Circular Dichroism of 9,10-Dihydrophenanthrene Derivatives Reveals both the Absolute Configuration and Conformation: A Novel Approach to Mislow's Helicity Rule

Stereoselective formation of a K-region dihydrodiol from phenanthrene by Streptomyces flavovirens

Enantiomeric Composition of the trans -Dihydrodiols Produced from Phenanthrene by Fungi

Contact Info

Product

Resources

About