Download Chemical and Biological Aspects of Steroid Conjugation by Seymour Bernstein, Samuel Solomon PDF

By Seymour Bernstein, Samuel Solomon

This booklet represents a collaborative pastime via a gaggle of investigators to assemble 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 $64000 box of bile acid and bile alcohol conjugation has been mentioned in simple terms superficially because it used to be made up our minds arbitrarily to be open air the projected scope of the booklet. The reader is pointed out the spouse quantity of this booklet, 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 information. additionally we want to convey our deep appreciation and gratitude to Mrs. Dorothy Budd, our copy-editor, and Mr. J. Joseph for his or her editorial tips in making this booklet attainable. SEYMOUR BERNSTEIN Pearl River, N. Y. January, 1970 SAMUEL SOLOMON V11 CONTENTS Preface . . . . VII Nomenclature a, dialogue of Nomenclature method x b, Trivial and Systematic Names. x checklist of individuals . . . . . . . . Xl Chemistry: Synthesis and Characterization S. BERNSTEIN, 1. P. DUSZA, and J. P. JOSEPH Enzymological features 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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The sulfation step involved the use of trimethylamine-sulfur trioxide complex in pyridine at room temperature for 18 hr to give the intermediate trimethylammonium salts. OH OH HO Na0 3 SO HO Na03S0 VII VIII s. : 32 Similarly these investigators [214] have synthesized sodium estral ,3,5( 1O)-triene-2,17 P-diol-2 -sulfate (X) [2-sulfooxyestra-1,3,5( 1O)-trien17 p-ol sodium salt] from the free phenol 17-acetate (IX). OAc HO l IX l) Me 3N· S03/Py 2) aq. NaOH OH Na03S0 X f) Triethylamine-Sulfur Trioxide.

The procedure was based on the method of Verley [164] for the preparation of phenol sulfate. Cholesterol (I) in chloroform solution was treated (15 min at room temperature, followed by 15 min at 50 0 ) with chI oro sulfonic acid in pyridine and chloroform. The intermediate, pyridinium salt (II) on treatment with base gives the corresponding metallic salt. Potassium hydroxide gave potassium cholesterol sulfate (III) in an 89 % over-all yield from cholesterol. (d)): Grant et al. 0 during the subsequent neutralization with N-methanolic sodium hydroxide.

Both 17fJ--estradiol-17-sulfate and estriol16,17-disulfate [160(,17fJ-disulfooxyestra-l,3,5(10)-trien-3-01] were prepared by hydrolysis of the completely sulfated derivatives (e. , XL VII) employing acid hydrolysis conditions, such as hydrochloric acid in aqueous methanol. These conditions were considered preferable to 70 % aqueous dioxane (60°). The extended hydrolysis of estriol-16,17-disulfate (XL VIII) resulted in the isolation of a mono sulfate which was identified as estriol-17-sulfate (XLIX) [17fJ-sulfooxyestra-l,3,5(lO)-triene-3,1 6cxdiol].

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