16-Diazoestrone

After stirring for 1 hr more, the reaction mixture is diluted with 500 ml of cold water the yellow precipitate which forms is filtered, washed and dried, to give 4.1 g (83%) of crude 16-diazoestrone methyl ether (94) mp 133-136°. Chromatography of the crude product over neutral alumina in chloroform, followed by recrystallization from chloroform-methanol, gives pure (94) mp 145-146°, in 64% over-all yield. ... 

N H2SO4 added with vigorous stirring at 0-5° to an aq. mixture of potassium 2-aminoestrone sulfate and NaNOg, after 2 min. the product quickly collected by filtration 2-diazoestrone sulfate. Y 12%. C.-C. Chin and J.C. Warren, Biochemistry 9, 1917 (1970). 

The two estrogen der y ives, 4-mercuriestradiol (4ME) and 2-diazoestrone sulfate (DZE) react rapidly with cysteine residues in glutamate dehydrogenase DZE also reacts with pyruvate kinase. Estradiol slows the rate of reaction of these derivatives, which is consistent with an affinity labeling mechanism. The reactivity and instability of these derivatives, however, limit their utility. 

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