This book represents a collaborative endeavor by a group of investigators to bring together in a single volume a critical discussion of the major facets of our knowledge, ranging from chemical to clinical aspects, of steroid conjugation. However, the important field of bile acid and bile alcohol conjugation has been discussed only superficially since it was decided arbitrarily to be outside the projected scope of the book. The reader is referred to the companion volume of this book, namely Physical Properties of Steroid Conjugates (by Bernstein, Dusza, and Joseph, Springer-Verlag New York 1968), for complemental information on individual conjugates. The Editors wish to thank Miss Elise Kramer for typing assistance. Also we wish to express our deep appreciation and gratitude to Mrs. Dorothy Budd, our copy-editor, and Mr. J. Joseph for their editorial assistance in making this book possible. Pearl River, N. Y. SEYMOUR BERNSTEIN January, 1970 SAMUEL SOLOMON V1l CONTENTS Preface. . . . VlI Nomenclature a, Discussion of Nomenclature System x b, Trivial and Systematic Names. x List of Contributors . . . . . . . . Xl Chemistry: Synthesis and Characterization S. BERNSTEIN, J. P. DUSZA, and J. P. JOSEPH Enzymological Aspects of Steroid Conjugation A. B. Roy . . . . . . . . . . 74 The Hydrolysis of Steroid Conjugates H. L. BRADLOW . * . * . 131 Isolation of Steroid Conjugates P. K. SUTERI. . . . . . . 182 The Biochemistry of the 3 p-Hydroxy-L1s-Steroid Sulfates K. D. ROBERTS and S. LIEBERMAN 219 Formation, Metabolism, and Transport of Estrogen Conjugates E. DICZFALUSY and M. LEVITZ. * . . * . . . . * . . .