Download e-book for kindle: Chemical and Biological Aspects of Steroid Conjugation by Seymour Bernstein, Samuel Solomon

By Seymour Bernstein, Samuel Solomon

ISBN-10: 3642951775

ISBN-13: 9783642951770

ISBN-10: 3642951791

ISBN-13: 9783642951794

This e-book represents a collaborative undertaking by way of a bunch of investigators to compile in one quantity a severe dialogue of the key elements of our wisdom, starting from chemical to medical facets, of steroid conjugation. despite the fact that, the real box of bile acid and bile alcohol conjugation has been mentioned in simple terms superficially because it was once made up our minds arbitrarily to be outdoors the projected scope of the ebook. The reader is mentioned the spouse quantity of this ebook, specifically actual homes of Steroid Conjugates (by Bernstein, Dusza, and Joseph, Springer-Verlag ny 1968), for complemental details on person conjugates. The Editors desire to thank pass over Elise Kramer for typing guidance. 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 advice 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 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. ok. SITTERI. . . . . . . 182 The Biochemistry of the 3P-Hydroxy-Ll5-Steroid Sulfates ok. D. ROBERTS and S. LIEBERMAN 219 Formation, Metabolism, and shipping of Estrogen Conjugates E. DICZFALUSY and M. LEVITZ. . . . . . . . . . . . .

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The sulfates were isolated as their sodium salts. Fex et al. [213] have utilized trimethylamine-sulfur trioxide complex for the preparation of sodium estriol-3-sulfate (VI) [3-sulfooxyestra1,3,5(1O)-triene-16 ct,17 [3-diol sodium salt] in 31 % conversion yield from estriol (IV). 3 N sodium hydroxide was heated at 55° for 7 hr with trimethylamine-sulfur trioxide complex. The intermediate trimethylammonium sulfate (V) was not characterized but treated with sodium acetate to give the desired compound.

BERNSTEIN et al. : 22 methyl ester derivative of the latter all gave similar ORD curves with a negative Cotton effect. Emiliozzi [105] has observed some anomalous results in the rotatory dispersion of the acetylated methyl ester glucuronide derivatives in the hydroxyandrostane series. 4. Infrared Absorption The companion volume of this work lists glucuronide conjugates for which infrared absorption data have been published by indicating such data to be available in the reference cited. In most cases this is confined to the listing of certain maximal absorption frequencies.

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


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