Abstract
A novel measuring method (electroimmunoassay) of 17β-estradiol (E 2) in urine or blood was proposed on the basis of a competition between E 2 and a labeled E 2 against an immobilizing antibody. To evaluate the principle, 3-{4-[17β-hydroxy-1,3,5(10)-estratrien-3-yloxy]butyldisulfanyl}- N-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxabenzocyclopentadecen-2-yl) succinamic acid ( 1 ) was designed and synthesized as a novel aminobenzo-15-crown-5-containing E 2 tethered with disulfide linkage. Two thiol-intermediates 5b and 19c were efficiently synthesized from mercaptosuccinic acid 7 and 4,4′-dithiodibutyric acid 12 , respectively. Formations of disulfide linkages from less reactive thiols were examined and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) could be employed for the formation of an unsymmetrical disulfide 20c from 5b and 19c . Then, removal of TMS- and allyl-protecting groups in 20c successfully afforded the crown ether-containing E 2 1 .
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