Michal Adamczyk

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A series of chemiluminescent 17beta-estradiol probes were synthesized. Relative equilibrium dissociation constants (K(D)) for the interaction of an anti-E(2) Fab fragment for the probes in solution were evaluated using a single E(2)-analog biosensor surface on a BIAcore surface plasmon resonance instrument. The results show the antibody fragment binds all(More)
O-(Acridinium)hydroxylamine (AHA) reacted with a representative sample of oxo-steroids (6-oxoestradiol, estrone, norethindrone, cortisol, progesterone, digoxin dialdehyde, and digitoxin dialdehyde) to produce chemiluminescent acridinium oxime (AO) conjugates in a single step in 37-68% yield after preparative HPLC.
The 5 and 6-isomers of O-(fluoresceinylmethyl)hydroxylamine reacted with a representative sample of oxo-steroids (6-oxoestradiol, estrone, norethindrone, cortisol, progesterone, and digitoxin-dialdehyde) to produce O-(fluoresceinylmethyl)oxime conjugates in a single step in 24-84% yield after preparative high performance liquid chromotography.
Amination of 3,17 beta-Bis[(2-trimethylsilylethoxy) methoxy]-1,3,5(10)-estratriene-6-one (2) using NaCNBH4 and NH4OAc afforded 3,17-bis(SEM)-6-aminoestradiol (3) as a mixture of alpha and beta-isomers in 60:40 ratio. Hydrolysis of the mixture of 3 using HF and separation by preparative high-performance liquid chromatography afforded pure 6(More)
6-Oxoestradiol (2) was protected as its bis[(2-trimethylsilylethoxy)methyl] ether (4) and converted to the corresponding oxime (4). The oxime (4) on reduction with zinc in ethanol afforded the bis-SEM ether of 6-alpha-aminoestradiol (5) in 96% epimeric excess. Subsequently, 5 was hydrolyzed with HF to 6-alpha-aminoestradiol (6) in good yield. The absolute(More)
Alkylation of 3,17 beta-bis(2-trimethylsilyl)ethoxymethyl-1,3,5(10) estratriene-6-one (2) with 5-bromo-1-pentene using NaHMDS in THF afforded 3,17 beta-bis(2-trimethylsilyl)ethoxymethyl-7-alpha-(4'pentenyl)-1,3,5(10) estratriene-6-one (3) in excellent stereoselectivity (> 95% epimeric excess). Functionalization of the side chain in compound 3 was(More)
Pure 3 alpha- and 3 beta-aminodigoxigenin were previously prepared from 12-acetyldigoxigenin by a multistep route involving tosylation, azide inversion, deprotection, and reduction. This paper describes the straightforward synthesis of the pure epimers in a single step via reductive amination of digoxigenone and chromatographic separation without the need(More)
Digoxin dialdehyde reportedly undergoes reductive amination with primary amines to form a perhydro-1,4-oxazepine; however, no structural proof has been published to substantiate this belief. A digoxin perhydro-1,4-oxazepine derivative has been isolated from the reductive amination of digoxin dialdehyde and its structure determined by mass spectroscopy and(More)
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