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PubMed2001

Metabolism of R,S enantiomers of 3-phenylamino-1,2-propanediol, a compound associated with the toxic oil syndrome, in C57BL/6- and A/J-strain mice.

PAP, a very polar substance, is highly metabolized in mice and excreted principally in urine in the form of the 2-hydroxy-3-phenylaminopropanoic acid of each enantiomer. Thus, the major route of PAP elimination in these strains is alkyl chain oxidation. In particular, S-PAP is eliminated principally in the form of that metabolite, whereas R-PAP enantiomer showed further oxidized species at the aromatic ring and alkyl chain, yielding potential decarboxylated compounds and iminoquinones. All these metabolites may have toxicologic implications. On the other hand, OOPAP intestinal hydrolysis in favour of one PAP enantiomer might be expected since lipases show chiral hydrolysis (unpublished data, manuscript in preparation). In this respect, enantiomeric distribution and metabolic differences should be taken into account in the toxicokinetics of these compounds and their potential association with Toxic Oil Syndrome symptoms.

Aniline Compounds↗
PubMedDate not supplied

[The synthesis of thio- and selenoanalogues of phospholipids on the basis of 2-butyl-2-hydroxymethyl-1,3-propanediol].

New analogues of nonglycerol polyol phospholipids were prepared on the basis of 1,1,1-trimethylolethane. Amidophosphites and cyclophosphites of the isopropylidene derivative of this polyol were intermediates in the syntheses. They were treated with sulfur or selenium. Phosphoacetals were converted into lipids by the direct acylation with higher fatty acid chlorides. The triol bicyclophosphite was also used in the lipid syntheses. It was directly acylated at the oxygen atom, the resulting acylpolyol of chlorophosphite was then converted into phospholipids by alcoholysis and subsequent treatment with sulfur.

Acetals↗