Circular dichroism spectra, optical rotations and absolute configurations of cis-dihydrodiol metabolites of quinoline and derivatives: the role of the nitrogen atom.
The absolute configurations of cis-dihydrodiol bacterial metabolites derived from quinoline substrates and their quinolinium salts have been determined by comparison of experimental and calculated chiroptical data (circular dichroism spectra and optical rotations). The role of intramolecular H-bonding and other interactions in the preferred conformations has been investigated, including the effect of protonation of several cis-dihydrodiols. The presence of a strong intramolecular OH...N bond in several cis-dihydrodiol metabolites suggests that such species have a residually chiral oxygen atom.
Kwit
Marcin
M
Department of Chemistry, A. Mickiewicz University, Poznan 60-780, Poland. Marcin.Kwit@amu.edu.pl
Gawronski
Jacek
J
Sbircea
Lenuta
L
Sharma
Narain D
ND
Kaik
Magdalena
M
Boyd
Derek R
DR
D002942:Circular Dichroism; D003198:Computer Simulation; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D009281:Naphthalenes / Q000737:chemistry* / Q000378:metabolism; D009584:Nitrogen / Q000737:chemistry*; D009904:Optical Rotation; D011804:Quinolines / Q000737:chemistry* / Q000378:metabolism; D013056:Spectrophotometry, Ultraviolet; D020578:Sphingomonas / Q000378:metabolism; D013237:Stereoisomerism; D013379:Substrate Specificity
D009281:Naphthalenes; D011804:Quinolines; C507866:trans-1,2-dihydro-1,2-naphthalenediol; D009584:Nitrogen