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Isolation and characterization of (+)-1,1a-dihydroxy-1-hydrofluoren-9-one formed by angular dioxygenation in the bacterial catabolism of fluorene.

Abstract：

:Transformation of fluorene by washed cells of fluorene-grown Pseudomonas sp. F274 yielded 1,la-dihydroxy-1-hydrofluoren-9-one (up to 100 mg/l) as the stable product of angular dioxygenation of 9-fluorenone. Structural identity of the angular keto-diol was established by 13C- and 1H-NMR, gas chromatography- and direct probe-mass spectrometry. Definitive assignment of 1,1a-dioxygenation, but not 4,4a-, was based on the isolation and rigorous identification of 1-hydroxyfluoren-9-one as the exclusive product of acidic dehydration. Chiral 1H-NMR analysis and optical rotation of isolated 1,1a-dihydroxy-1-hydrofluoren-9-one ([alpha]D = + 132.1 degrees) are indicative of a single enantiomer with an inferred cis-stereochemistry of the hydroxyl groups. This compound is evidently an intermediate of fluorene catabolism by this strain and not a dead-end product because its formation is transient in washed cell incubations and ultimately it is completely consumed with the formation of acidic metabolites.

journal_name

Biochem Biophys Res Commun

journal_title

Biochemical and biophysical research communications

authors

Selifonov SA,Grifoll M,Gurst JE,Chapman PJ

doi

10.1006/bbrc.1993.1591

subject

Has Abstract

pub_date

1993-05-28 00:00:00

pages

67-76

issue

1

eissn

0006-291X

issn

1090-2104

pii

S0006-291X(83)71591-3

journal_volume

193

pub_type

杂志文章

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