Allergenic alpha-methylene-gamma-butyrolactones. Stereospecific syntheses of (+)- and (-)-gamma-methyl-alpha-methylene-gamma-butyrolactones. A study of the specificity of (+) and (-) enantiomers in inducing allergic contact dermatitis.
J Med Chem
; 25(8): 943-6, 1982 Aug.
Article
em En
| MEDLINE
| ID: mdl-7120282
ABSTRACT
The enantiomers of gamma-methyl-alpha-methylene-gamma-butyrolactone have been prepared stereospecifically from (R)- and (S)-glutamic acid. Three groups of guinea pigs have been sensitized (Feund complete adjuvant technique) to the (+) isomer, the (-) isomer, and the (+/-) mixture. The animals have been tested with each of the enantiomers and with a mixture of the compounds. Only the (-) enantiomer showed some specificity guinea pigs sensitized to this enantiomer react weakly to the other compound; in turn, animals sensitized to the (+) enantiomer react similarly to both antipodes. Interestingly, reaction to the (+/-) mixture in each group of guinea pigs was the sum of skin responses to the individual enantiomer. These results should be contrasted with sensitization to (+)- and (-)-frullanolides, sesquiterpene lactones for which strong stereospecificity was observed.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
4-Butirolactona
/
Alérgenos
/
Dermatite de Contato
/
Furanos
Limite:
Animals
Idioma:
En
Ano de publicação:
1982
Tipo de documento:
Article