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 publication represents a collaborative undertaking via a bunch of investigators to compile in one quantity a serious dialogue of the most important aspects of our wisdom, starting from chemical to scientific facets, of steroid conjugation. notwithstanding, the real box of bile acid and bile alcohol conjugation has been mentioned purely superficially because it was once made up our minds arbitrarily to be outdoor the projected scope of the ebook. The reader is spoke of the better half quantity of this publication, specifically actual homes of Steroid Conjugates (by Bernstein, Dusza, and Joseph, Springer-Verlag big apple 1968), for complemental details on person conjugates. The Editors desire to thank leave out Elise Kramer for typing guidance. additionally we want to show 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 publication 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 facets 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 ok. D. ROBERTS and S. LIEBERMAN 219 Formation, Metabolism, and shipping of Estrogen Conjugates E. DICZFALUSY and M. LEVITZ. . . . . . . . . . . . .

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Levitz [183] has reported on the synthesis of 6,7-3H-estrone sulfate and estrone-3s S-sulfate by use of the pyridine sulfate method of Sobel, Drekter, and Natelson [182] and noted that the sulfuric acid containing 3SS is inexpensive and safe to handle. In the presence of a 10% molar excess of acetic anhydride, pyridine sulfate reacted with estrone overnight at room temperature to produce pyridinium estrone sulfate in good yield. Without isolation, the latter was converted into sodium estrone sulfate by the addition of sodium hydroxide.

Column hydrolysis of steroid glucuronides was observed and thus the mass spectrum records the molecular ion of the parent steroid. Successful resolution of this problem has been reported by several groups of workers [138140]. The approach is essentially the same in that the glucuronide fraction or pure compound is esterified with diazomethane. Etherification of the remaining hydroxyl groups with hexamethyldisilazane and trimethylchlorosilane affords a derivative which appears to be stable to glc conditions.

The observed optical rotations of the compounds were compared with the calculated values for the 0(-0- and fJ-o-configurations. The observed figures agreed closely with the fJ-ostructure in all four cases. The calculated figures were derived from the Klyne rule for steroid glycosides [143] which was modified by the replacement of the glycosyl by glucuronyl term. The validity of this modified Klyne rule was checked against the rotation of three acetylated derivatives of 3-hydroxysteroids recorded in the literature.

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


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