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.
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.
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D000485:Allergens / Q000138:chemical synthesis*; D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D003877:Dermatitis, Contact / Q000209:etiology* / Q000276:immunology; D005620:Freund's Adjuvant / Q000494:pharmacology; D005663:Furans / Q000138:chemical synthesis*; D006168:Guinea Pigs; D008968:Molecular Conformation; D013237:Stereoisomerism
D000485:Allergens; D005663:Furans; C014096:alpha-methylene gamma-butyrolactone; D005620:Freund's Adjuvant; D015107:4-Butyrolactone