Synthesis of 17 beta-hydroxyandrost-4-en-3-one-7 alpha-(biotinyl-6-N-hexylamide), a conjugate useful for affinity chromatography and for testosterone immunoassays.

  title={Synthesis of 17 beta-hydroxyandrost-4-en-3-one-7 alpha-(biotinyl-6-N-hexylamide), a conjugate useful for affinity chromatography and for testosterone immunoassays.},
  author={Peter Luppa and S Hauck and I Schwab and Christian Birkmayer and Hagen Hauptmann},
  journal={Bioconjugate chemistry},
  volume={7 3},
We describe the synthesis of 17 beta-hydroxyandrost-4-en-3-one-7 alpha-(biotinyl-6-N-hexylamide) from 17 beta-hydroxyandrost-4-en-3-one (testosterone) via copper-catalyzed 1,6 Michael addition of a 6-(tertbutyldimethylsilyloxyhexyl) chain to 6-dehydrotestosterone 17 beta-acetate. After chromatographic separation of the 7 alpha-isomer from the alpha / beta mixture and cleavage of the silyl ether, the alcohol was oxidized to the 6-hexanal side chain and then subjected to reductive amination. The… 
9 Citations
Synthesis of 15β-hydroxyalkyl-substituted (17Z)-pregn-17-enes, their ethers and esters
Proceeding from Δ15-17-ketosteroids via copper(I)-catalyzed 1,4-addition of Grignard reagent followed by modification of the 15-alkenyl substituent, introduction of a 17-ethylidene component via
Synthesis of Oxorhenium(V) Complexes Derived from 7α-Functionalized Testosterone: First Rhenium-Containing Testosterone Derivatives
The first oxorhenium(V) complexes containing a pendant testosterone moiety are synthesized and the α-stereoselectivity is governed by the presence of the C-19 methyl group.
7 alpha-Biotinylated testosterone derivatives as tracers for a competitive chemiluminescence immunoassay of testosterone in serum.
The optimized steric structure and the long spacer arm of the biotinylated testosterone tracer make this chemiluminescence assay well-suited for measuring total testosterone concentration in serum, demonstrating the favorable specificity of the combination of a "nearly native" tracer with a position analog antibody.
Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents
Reductive amination is an important tool for synthetic organic chemists in the construction of carbon-nitrogen bonds. This reaction, also termed reductive alkylation, involves condensation of an
Bisphenol A directly targets tubulin to disrupt spindle organization in embryonic and somatic cells.
Treatment of mammalian cells demonstrated that BPA as well as a series of Bisphenol A derivatives induced ectopic spindle pole formation in the absence of centrosome overduplication, suggesting a novel mechanism by which BPA affects the nucleation of microtubules, disrupting the tight spatial control associated with normal chromosome segregation.
ABBREVIATIONS ............................................................................................................... 219 INTRODUCTION
Analysis of Androgens and Their Derivatives
In view of the enormous increase in the field of androgens during the past decade, an important decision had to be made concerning this present revised chapter. Some of the older material, prior to