Synthesis of buprestins D, E, F, G and H; structural confirmation and biological testing of acyl glucoses from jewel beetles (Coleoptera: Buprestidae).
A chemical and enzymatic synthesis was developed for five variant buprestins termed D, E, F, G and H found in jewel beetles (Coleoptera: Buprestidae). Selective acylation of the primary hydroxyl group of beta-D-glucopyranose-1,2-bis(pyrrole-2-carboxylate) with substituted benzoic or cinnamic acid derivatives followed by deprotection gave the target compounds. Using coinjection the identity with the natural extracts was confirmed. The activity of the variant buprestins as deterrents for ants was assayed.
Ryczek
Sebastian
S
Bioorganische Chemie, Gebäude NWI, Universität Bayreuth, 95440 Bayreuth, Germany.
Dettner
Konrad
K
Unverzagt
Carlo
C
D000215:Acylation; D000818:Animals; D002934:Cinnamates / Q000737:chemistry; D001517:Coleoptera / Q000737:chemistry*; D005947:Glucose / Q000031:analogs & derivatives / Q000737:chemistry* / Q000302:isolation & purification; D006601:Hexoses / Q000138:chemical synthesis; D007302:Insect Repellents / Q000138:chemical synthesis / Q000737:chemistry
D002934:Cinnamates; D006601:Hexoses; D007302:Insect Repellents; C029010:cinnamic acid; D005947:Glucose