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Title

Studies on toxic oil syndrome: stereoselective hydrolysis of 3-(phenylamino)propane-1,2-diol esters by human pancreatic lipase

AuthorsMorató, Anna; Martínez-Cabot, Anna; Escabrós, Jordi; Bujons Vilàs, Jordi; Messeguer Peypoch, Ángel CSIC ORCID
KeywordsToxic Oil Syndrome
3-phenylamino-1,2-propanediol
PAP
Human pancreatic lipase
Lipase incubations
Issue Date28-May-2004
PublisherAmerican Chemical Society
CitationChemical Research in Toxicology 17(7): 889–895 (2004)
AbstractThe ingestion of rapeseed oil batches denatured with aniline and illegally refined and distributed by street vendors was responsible for toxic oil syndrome (TOS), an intoxication episode that took place in Spain in 1981, causing over 400 deaths and affecting more than 20 000 people. Despite the intense research efforts carried out to date, the compounds responsible for that intoxication have not been elucidated. Nevertheless, epidemiological studies have pointed to fatty acid mono- and diesters of 3-phenylamino-1,2-propanediol (PAP) as the biomarkers of those toxic oil batches. The structure of these esters bears common features with that of triglycerides, which suggested that PAP esters could follow the route of lipids metabolism up to a certain extent. The incubation of racemic PAP dioleyl ester with human pancreatic lipase (hPL) led to the formation of the corresponding stereoisomeric monoesters bearing the oleyl residue at C-2, although a kinetic resolution in favor of the (S)-enantiomer was observed. These monoesters are unstable and in equilibrium with their corresponding regioisomers with the acyl residue at C-1, apparently without the intervention of the lipase. Finally, incubations of these latter monoesters with hPL led to the formation of the respective PAP enantiomers. Again, the kinetic resolution of this hydrolytic process favored the formation of the enantiomer with the (S)-configuration. Taken together, these results showed that PAP esters are substrates of hPL and that the two hydrolytic steps exhibit kinetic resolution in favor of the (S)-enantiomers.
Description7 pages, 5 figures, 2 charts, 1 table.-- PMID: 15257613 [PubMed].-- Printed version published Jul 15, 2004.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/tx049952z
Publisher version (URL)http://dx.doi.org/10.1021/tx049952z
URIhttp://hdl.handle.net/10261/17981
DOI10.1021/tx049952z
ISSN0893-228X
E-ISSN1520-5010
Appears in Collections:(IQAC) Artículos

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