Luppa, Peter and Birkmayer, Christian and Hauptmann, Hagen (1994) SYNTHESIS OF 3-HYDROXYESTRA-1,3,5(10)-TRIEN-17-ONE AND 3,17-BETA-DIHYDROXYESTRA-1,3,5(10)-TRIENE 6-ALPHA-N-(EPSILON-BIOTINYL)CAPROAMIDE, TRACER SUBSTANCES FOR DEVELOPING IMMUNOASSAYS FOR ESTRONE AND ESTRADIOL. BIOCONJUGATE CHEMISTRY, 5 (2). pp. 167-171. ISSN 1043-1802
Full text not available from this repository.Abstract
We describe the synthesis of 3-hydroxyestra-1,3,5(10)-trien-17-one 6alpha-N-(epsilon-biotinyl)caproamide and 3,17beta-dihydroxyestra-1,3,5(10)-triene 6alpha-N-(epsilon-biotinyl)caproamide from 3-hydroxyestra-1,3,5(10)-trien-17-one and 3,17 beta-dihydroxyestra-1,3,5(10)-triene, via the 6-keto estrogenic derivatives. The reductive amination of these compounds is an effective step toward an epimeric mixture of the respective amines, which are easily biotinylated by use of N-(epsilon-biotinylcaproyl)-N-hydroxysuccinimide ester. The 6alpha-epimers could be isolated from the alpha/beta-composition by application of isocratic HPLC, and overall yields were about 20% for the epimeric end products. The structures of the stereoisomers could clearly be assigned through H-1 NMR studies. The ratios of the respective isomers obtained from the reductive amination were found to be 3(alpha):2(beta). The biotinylated estrogens can be used as tracers in a novel immunoassay concept for the determination of these analytes in human serum. Ring position 6 was selected for derivatization because of its distance from the functionalized positions 3 and 17 and, therefore, of a negligible alteration of the tracer's structure in comparison to underivatized estrone or estradiol.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | CHEMI-LUMINESCENCE IMMUNOASSAY; SOLID-PHASE ENZYMOIMMUNOASSAY; ANTIBODY; BINDING; SERUM; ESTRONE-3-GLUCURONIDE; CONJUGATE; COMPLEX; ELISA |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Petra Gürster |
| Date Deposited: | 10 Sep 2024 06:27 |
| Last Modified: | 10 Sep 2024 06:27 |
| URI: | https://pred.uni-regensburg.de/id/eprint/53425 |
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