Chemical and enzyme-catalysed synthesis of quinoline arene hydrates.
Arene hydrates of quinoline have been synthesized by enzyme-catalysed benzylic and allylic hydroxylation of dihydroquinolines in growing cultures of the fungus Mortierella isabellina and in liver microsomal preparations. A preference for allylic hydroxylation was generally observed in eukaryotic systems. Evidence of epoxidation of dihydroarenes by both the fungal and animal enzyme systems was also obtained. The chemical synthesis of these arene hydrates (5-hydroxy-5,6-dihydroquinoline, 6-hydroxy-5,6-dihydroquinoline, 7-hydroxy-7,8-dihydroxyquinoline, and 8-hydroxy-7,8-dihydroquinoline) from the corresponding hydroxy-5,6,7,8-tetrahydroquinolines, has also been accomplished.
Agarwal
R
R
School of Chemistry, Queen's University of Belfast, U.K.
Boyd
D R
DR
Sharma
N D
ND
McMordie
R A
RA
Porter
H P
HP
van Ommen
B
B
van Bladeren
P J
PJ
D000818:Animals; D008401:Gas Chromatography-Mass Spectrometry; D006900:Hydroxylation; D006912:Hydroxyquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008748:Methylcholanthrene / Q000494:pharmacology; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism*; D015394:Molecular Structure; D009090:Mucorales / Q000378:metabolism*; D010634:Phenobarbital / Q000494:pharmacology; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry
D006912:Hydroxyquinolines; D011804:Quinolines; D008748:Methylcholanthrene; D010634:Phenobarbital