PMID: 9558712Apr 29, 1998Paper

Synthesis of 6 beta-aminoestradiol and its biotin, acridinium, and fluorescein conjugates

Steroids
M AdamczykR E Reddy

Abstract

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 beta-aminoestradiol (4) in good yield. The relative stereochemistry of the amino group in 4 was established by NMR. The biotinylated estradiol probe (7), chemiluminescent probe (9), and fluorescent probe (11), were prepared from 6 beta-aminoestradiol (4) and the corresponding biotin, 10-(3-sulfopropyl)-N-tosyl-N-(3-carboxypropyl)acridinium-9-carboxamide, and 5-carboxyfluorescein N-succinimidyl esters in 43-63% yields and > 99% purity.

References

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Citations

Apr 20, 2002·Bioorganic & Medicinal Chemistry Letters·Maciej AdamczykZhiguang Yu
Feb 18, 1999·Bioorganic & Medicinal Chemistry Letters·M AdamczykP G Mattingly
Aug 20, 2005·Asian Journal of Andrology·Mukhtar AleemManjeet Gill-Sharma
Mar 5, 2002·Analytical Sciences : the International Journal of the Japan Society for Analytical Chemistry·Tomoyuki OeToshimasa Toyo'oka
Feb 10, 2019·Steroids·Nisal Gajadeera, Robert N Hanson

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