William Charney

Microbiological transformation of steroids—X: 1-dehydro analogs of cortical steroids

Abstract The transformation of the principal adrenocortical ormones into the corresponding 1-dehydro analogs by the action of Corynebacterium simplex (A.T.C.C. 6946) is described.

Microbiological transformation of steroids—XI : The action of corynebacterium simplex on non-corticoid steroid substrates

Abstract Corynebacterium simplex (A.T.C.C. 6946) causes the following reactions to occur with appropriate steroid substrates: (1) oxidation of Δ5-3β-hydroxyl to Δ4-3-ketone, (2) oxidation of Δ5-3β-hydroxyl to Δ1,4-diene-3-ketone, (3) oxidation of secondary 17β-hydroxyl to 17-ketone, (4) oxidation of 20β-hydroxyl to 20-ketone, (5) oxidation of 19-nor-Δ4-3-ketone to Δ1,3,5 (10)-triene-3-hydroxyl and (6) hydrolysis of 3- and 21-acetate groups.

THE CONSTRUCTION AND USE OF

Publisher Summary This chapter presents the table I in which the entries are all products of microbial transformation. With few exceptions, compounds are recorded in this table only when a detailed procedure has been given in the cited reference. Products of known empirical formula, but unknown structure, are shown at the end of each group of entries having common empirical formulas. Systematic organic chemical nomenclature has been used, except for sapogenins and steroidal alkaloids. Common names of the principal hormones are given parenthetically. Configuration of any substituent attached to a ring carbon of the steroid nucleus is defined as β when that substituent projects above the plane of the steroid nucleus and as α when the substituent projects below the plane. Substituents that have the β-configuration are shown attached to the nucleus by solid lines, and those which have α configuration, by dotted lines. Configuration of hydrogen at the 5-position is always defined by 5 α- or 5 β-preceding the stem.

THE CONSTRUCTION AND USE OF – TRANSFORMATIONS BY GENUS

Publisher Summary This chapter presents the table III in which the entries include all the genera, species, sources, substrates, and reactions reported in the cited references. These include both inactive genera and assignments for reactions based solely on chromatographic evidence. Transformations that are documented with specific experimental details are cross-indexed with the product table. Occasional changes in spelling were made to conform to standard reference texts or culture collection catalogs. Systematic organic chemical nomenclature has been used, in most entries, except for sapogenins and steroidal alkaloids. There is no more than one class of suffix designation for substituents that is affixed to any stem.

CHAPTER IV – TAXONOMY

Publisher Summary This chapter presents a system of classification that is designed as an aid to determine the taxonomic position and relationships of the genera, active and inactive, that have been used for the transformations of steroids. Generally, the same groupings or categories have been used for classifications of bacteria and fungi as have been used for plants. The classes, orders, families, genera, and species in the various tables are listed alphabetically for convenience and, therefore, may not be in the same sequence as would be found in various published systems of taxonomy. The chapter presents the table II that is a taxonomic listing for reference purposes containing all cultures reported in the literature and U.S. patents through January, 1964. This spectrum of genera encompasses all five classes of microorganisms, the Ascomycetes, Basidiomycetes, Fungi Imperfecti, Phycomycetes, and Schizomycetes, 23 out of 49 major orders, 292 different genera, and 1216 different species. The most widely screened taxonomic class has been the Fungi Imperfecti. 111 of the 292 genera listed in the table and 534 of the 1216 species are members of the Fungi Imperfecti.

CHEMICAL CLASSIFICATION OF MICROBIAL TRANSFORMATIONS OF STEROIDS

Publisher Summary Microbial transformations of steroids are part of the larger class of organic chemical reactions that are catalyzed by enzymes. The microorganisms function as a convenient source of the required enzymes and, in some cases, provide identifiable reagent species that act on the steroid in the presence of the enzyme or contribute to the regeneration of the active site on the enzyme. The fact that the reactions are indeed enzymatic has been proved in several cases by the isolation of the crystalline enzyme from the microbial species and by the subsequent transformation of the steroid in vitro, using the crystalline enzyme and an added reagent. The resulting transformation was identical with that obtained employing the intact microbial system with the same substrate. This chapter discusses the chemical classification of microbial transformations of steroids, classes of chemical reactions, esterification of steroid alcohols, and hydrolysis of oxides to alcohols. It also discusses some of the reaction classes, such as Wagner–Meerwein rearrangement, decarboxylation, aldol and reverse aldol reactions, and Michael addition.