title: New steroid haptens for radioimmunoassay: synthesis of steroids substituted with thioether or ester linkages at the 2 alpha-position.
abstract: Haptens with bridge at the 2-position have not yet been explored. Radioimmunoassays with antibodies directed against 2 alpha-alkyl bridged steroid haptens are expected to be highly specific due to greater topographical exposure and similarity in conformation to the native steroid. The 2 alpha-alkyl bridged haptens were synthesized by first adding a cyclopropane ring to 2-methylene-4-en-3-one. Selective opening of the three-membered ring with trimethyl silyl iodide and transformation of the iodo group gave a carbocyclic acid, the desired analog for conjugation with protein.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Bombay.
authors.forename: U R
authors.initials: UR
authors.lastname: Desai
authors.forename: G K
authors.initials: GK
authors.lastname: Trivedi
mesh_terms: D000918:Antibody Specificity; D055598:Chemical Phenomena; D002621:Chemistry; D013196:Dihydrotestosterone / Q000276:immunology; D004951:Esterification; D006241:Haptens / Q000276:immunology*; D007106:Immune Sera / Q000276:immunology; D007651:Keto Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000276:immunology; D007653:Ketocholesterols / Q000138:chemical synthesis / Q000737:chemistry / Q000276:immunology; D008968:Molecular Conformation; D015394:Molecular Structure; D011422:Propionates; D011863:Radioimmunoassay; D013256:Steroids / Q000138:chemical synthesis / Q000276:immunology*; D013387:Succinic Anhydrides; D013438:Sulfhydryl Compounds
chemical_list: D006241:Haptens; D007106:Immune Sera; D007651:Keto Acids; D007653:Ketocholesterols; D011422:Propionates; D013256:Steroids; D013387:Succinic Anhydrides; D013438:Sulfhydryl Compounds; D013196:Dihydrotestosterone; C070234:7-(3-oxocholest-4-en-2-yl)-5-oxa-4-oxoheptanoic acid; C017526:3-methylthiopropionate; C031801:succinic anhydride