The therapeutic efficacy
of bioactive compounds is related to their
bioavailability. In turn, the bioavailability depends on the equilibrium
between the hydrophilicity and the lipophilicity. 2(
R,S
)-(Polyhydroxyalkyl)thiazolidine-4(
R
) carboxylic
acids (TCAs), obtained from the condensation of
l
-cysteine
and an aldose, have been recognized as nontoxic precursors of glutathione
with important preventive and therapeutic effects. The bioavailability
of these compounds can be improved by enhancing their lipophilicity.
This can be achieved by the introduction of some acyl groups derived
from fatty acids via esterification of the aldose hydroxyl groups.
With this purpose four new compounds were synthesized through a selective
palmitoyl acylation of
d
-(−)-ribose and
d
-(+)-glucose and subsequent condensation with
l
-cysteine.
In addition, the log P of the new compounds was calculated as a measure
of the lipophilicity, and in vitro 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic
acid) tests were performed as a measure of the antioxidant capability.
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