By Seymour Bernstein, Samuel Solomon
This booklet represents a collaborative recreation through a gaggle of investigators to compile in one quantity a serious dialogue of the foremost features of our wisdom, starting from chemical to medical elements, of steroid conjugation. even if, the real box of bile acid and bile alcohol conjugation has been mentioned purely superficially because it used to be determined arbitrarily to be outdoors the projected scope of the e-book. The reader is talked about the better half quantity of this e-book, specifically actual homes of Steroid Conjugates (by Bernstein, Dusza, and Joseph, Springer-Verlag ny 1968), for complemental info on person conjugates. The Editors desire to thank omit Elise Kramer for typing assistance. additionally we want to exhibit our deep appreciation and gratitude to Mrs. Dorothy Budd, our copy-editor, and Mr. J. Joseph for his or her editorial counsel in making this ebook attainable. SEYMOUR BERNSTEIN Pearl River, N. Y. January, 1970 SAMUEL SOLOMON V11 CONTENTS Preface . . . . VII Nomenclature a, dialogue of Nomenclature procedure x b, Trivial and Systematic Names. x record of participants . . . . . . . . Xl Chemistry: Synthesis and Characterization S. BERNSTEIN, 1. P. DUSZA, and J. P. JOSEPH Enzymological points of Steroid Conjugation A. B. Roy . . . . . . . . . . seventy four The Hydrolysis of Steroid Conjugates H. L. BRADLOW . . . . . 131 Isolation of Steroid Conjugates P. okay. SITTERI. . . . . . . 182 The Biochemistry of the 3P-Hydroxy-Ll5-Steroid Sulfates okay. D. ROBERTS and S. LIEBERMAN 219 Formation, Metabolism, and shipping of Estrogen Conjugates E. DICZFALUSY and M. LEVITZ. . . . . . . . . . . . .
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Extra info for Chemical and Biological Aspects of Steroid Conjugation
Sulfation of the 6f3-hydroxyl group in LJ4-3-one steroids does not impose any additional effect on the LJ 4-3-one chromophore from that of the normal hypsochromic effect of the 6f3-hydroxyl group and decrease in extinction coefficient associated with that grouping . The ultraviolet spectra of several alkyl and aryl steroid sulfates have been recorded in concentrated sulfuric acid . When compared to their un sulfated counterparts no difference could be detected. The time study curves of each pair were also indistinguishable.
As a result of its stability, this complex may be used without regard for anhydrous conditions. Moreover, it may be used as a sulfating agent in aqueous solutions. Usually, loss of this reagent by hydrolysis is minor since the rate of sulfation is much faster. Hydorn, Lerner, and Schwartz  were the first to report the use of trimethylamine-sulfur trioxide as a sulfating agent in the steroid field. The 21-sulfate of triamcinolone acetonide [9 ct-fluoro-ll [3,21-dihydroxy16 ct, 17 ct-isopropylidenedioxypregn -1 ,4-diene-3,20-dione] and its Ring A-saturated analog were prepared with the reagent in pyridine at room temperature.
The triethylammonium sulfates were found to be, generally, highly crystalline compounds which could be readily recrystallized. Analytical data indicated the salts to be generally nonhydrated, nonhygroscopic, and stable under normal storage conditions. An advantage of the triethylammonium salts is their solubility in methylene chloride which conveniently allows their recrystallization from methylene chloride-anhydrous ether. ), removes colored impurities and, in some cases, unreacted starting material.