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(Received for publication, October 21, 1996, and in revised form, December 17, 1996)
§
,§
,
and
From the The development of tolerance in Pseudomonas
putida DOT-T1 to toluene and related highly toxic compounds
involves short- and long-term responses. The short-term response is
based on an increase in the rigidity of the cell membrane by rapid
transformation of the fatty acid cis-9,10-methylene
hexadecanoic acid (C17:cyclopropane) to unsaturated
9-cis-hexadecenoic acid (C16:1,9 cis) and
subsequent transformation to the trans isomer. The
long-term response involves in addition to the changes in fatty acids,
alterations in the level of the phospholipid polar head groups:
cardiolipin increases and phosphatidylethanolamine decreases. The two
alterations lead to increased cell membrane rigidity and should be
regarded as physical mechanisms that prevent solvent penetrance.
Biochemical mechanisms that decrease the concentration of toluene in
the cell membrane also take place and involve: (i) a solvent exclusion system and (ii) metabolic removal of toluene via oxidation. Mutants unable to carry out cis 
Department of Organic Chemistry,
University of Granada, 18012 Granada, Spain and the
§ Department of Biochemistry, Consejo Superior de
Investigaciones Científicas, Estación Experimental de
Zaidín, 18012 Granada, Spain
trans isomerization
of unsaturated lipids, that exhibit altered cell envelopes because of
the lack of the OprL protein, or that are unable to exclude toluene
from cell membranes are hypersensitive to toluene.
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