The isolation and identification of 6-hydroxycyclohepta-1,4-dione as a novel intermediate in the bacterial degradation of atropine.
Growth of Pseudomonas AT3 on the alkaloid atropine as its sole source of carbon and nitrogen is nitrogen-limited and proceeds by degradation of the tropic acid part of the molecule, with the metabolism of the tropine being limited to the point of release of its nitrogen. A nitrogen-free compound accumulated in the growth medium and was isolated and identified as 6-hydroxycyclohepta-1,4-dione. This novel compound is proposed as an intermediate in tropine metabolism. It served as a growth substrate for the organism and was also the substrate for an NAD(+)-linked dehydrogenase present in cell extracts. The enzyme was induced during the tropine phase of diauxic growth on atropine or during growth on tropine alone.
Bartholomew
B A
BA
Department of Biochemistry, University of Wales, Aberystwyth, Dyfed, U.K.
Smith
M J
MJ
Long
M T
MT
Darcy
P J
PJ
Trudgill
P W
PW
Hopper
D J
DJ
D000429:Alcohol Oxidoreductases / Q000378:metabolism; D001285:Atropine / Q000378:metabolism*; D002855:Chromatography, Thin Layer; D003508:Cycloheptanes / Q000737:chemistry / Q000302:isolation & purification*; D010666:Phenylpropionates / Q000378:metabolism; D011549:Pseudomonas / Q000254:growth & development* / Q000378:metabolism; D014326:Tropanes / Q000378:metabolism
D003508:Cycloheptanes; D010666:Phenylpropionates; D014326:Tropanes; C082133:6-hydroxycyclohepta-1,4-dione; D001285:Atropine; C005864:tropine; C011377:tropic acid; D000429:Alcohol Oxidoreductases; C082135:6-hydroxycyclohepta-1,4-dione dehydrogenase