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Archives of Biochemistry and Biophysics | 1963

MICROBIAL FORMATION AND HYDROLYSIS OF TESTOLOLACTONE.

C.E. Holmlund; Robert H. Blank; Karl J. Sax; Ralph H. Evans

Abstract Testolic acid has been isolated and identified as the major final product from the fermentation of androstenedione with Cephalosporium acremonium . The occurrence of testolic acid in fermentations with other microorganisms reported to produce testololactone is noted. Testolic acid is produced by enzymatic hydrolysis of testololactone and is probably not a precursor in the microbiological formation of testololactone.


Steroids | 1965

Microbiological formation of 1α,2α-dihydroxysteroids

Karl J. Sax; C.E. Holmlund; Louis I. Feldman; R.H. Evans; Robert H. Blank; A.J. Shay; J.S. Schultz; M. Dann

Abstract Selected steroids give rise to 1α,2α-dihydroxylated products when fermented with nocardia corallina (ATCC 999). Preparation of the 1α,2α-dihydroxy derivatives of 17α-ethynyl-17β-hydroxyandrost-4-en-3-one (I), 9α-fluoro-11β,17β-dihydroxy-17α-methylandrost-4-en-3-one (VI), and 11β,21-dihydroxy-16α,17α-isopropylidenedioxypregn-4-ene-3,20-dione (XII) is described. Induction of the required enzymes by prior exposure of N. corallina to androstenedione was necessary to obtain the 1α,2α-dihydroxy products from I and XII.


Journal of Organic Chemistry | 1952

Δ5, 7-Steroids. XII.1, 2 Steroidal Cyclic Ketals. I. Cyclic Ketals of Δ4, 7-3-Ketosteroids

Rose Antonucci; Seymour Bernstein; Ruddy Littell; Karl J. Sax; James H. Williams


Journal of Organic Chemistry | 1951

Δ5, 7-Steroids. VII. The Conversion of Δ5, 7- to Δ5, 7, 9-Steroidal Hormones

Rose Antonucci; Seymour Bernstein; Dominic Giancola; Karl J. Sax


Journal of Organic Chemistry | 1951

Δ5, 7-Steroids. VI. The Preparation of Δ5, 7-Steroidal Hormones

Rose Antonucci; Seymour Bernstein; Dominic Giancola; Karl J. Sax


Journal of Organic Chemistry | 1952

Δ5,7-Steroids. XIII. Steroidal Cyclic Ketals. II1,2the Preparation of Δ4,7-Pregnadiene-3,20-Dione and Δ4,7-Pregnadiene-21-Ol-3,20-Dione-Acetate

Rose Antonucci; Seymour Bernstein; Robert H. Lenhard; Karl J. Sax; James H. Williams


Journal of Organic Chemistry | 1962

Stereospecific Oxidation of a Methylthio Steroid to the Sulfoxide by Calonectria decora

C. E. Holmlund; Karl J. Sax; B. E. Nielsen; R. E. Hartman; R. H. Evans; Robert H. Blank


Journal of Organic Chemistry | 1951

Δ5, 7-STEROIDS. V. (1). 7-DEHYDROCHOLESTERYL MERCAPTAN

Seymour Bernstein; Karl J. Sax


Journal of Organic Chemistry | 1977

Enzymatic and chemical resolution of 1-octyn-4-ol.

William J. McGahren; Karl J. Sax; Martin P. Kunstmann; George A. Ellestad


Journal of Organic Chemistry | 1964

Microbiological 16-Oxidation of Estr-4-en-3-one

Karl J. Sax; Robert H. Blank; R. H. Evans; Louis I. Feldman; C. E. Holmlund

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