Microbial hydroxylation of steroids. 5. Metabolism of androst-5-ene-3,17-dione and related compounds by Rhizopusarrhizus ATCC 11145

1979 ◽  
Vol 57 (4) ◽  
pp. 436-440 ◽  
Author(s):  
Herbert L. Holland ◽  
Peter R. P. Diakow
Keyword(s):  
Rhizopus Arrhizus ◽  
Microbial Hydroxylation ◽  
Related Compounds

The products of the incubation of androst-5-ene-3,17-dione (2a), 3β-hydroxyandrost-5-ene-17-one (2b), and androsta-3,5-diene-17-one (3) with Rhizopus arrhizus ATCC 11145 under a variety of conditions have been identified and the mechanisms of their formation discussed. In addition, several C-(4,5)- and C-(5,6)-epoxyandrostanes have been incubated with R. arrhizus, the products identified and possible pathways for their formation presented.

The Mechanism of the Microbial Hydroxylation of Steroids. Part 2. Hydroxylation of a Δ4-3-Ketosteroid Analog by Rhizopus arrhizus ATCC 11145

1975 ◽  
Vol 53 (14) ◽  
pp. 2041-2044 ◽  
Author(s):  
Herbert L. Holland ◽  
Barbara J. Auret
Keyword(s):  
Transition State ◽  
Rhizopus Arrhizus ◽  
Microbial Hydroxylation ◽  
Microbial C

The Δ4-3-ketosteroid analog (± )-4a-methyl-4,4a,5,6,7,8-hexahydro-2(3H) naphthalenone (1) is hydroxylated at both C-8α and C-8β by Rhizopusarrhizus ATCC 11145. The ratio of C-8α to C-8β hydroxylation is compared with that obtained from the peracid oxidation of 2-ethoxy-4a-methyl-3,4,4a,5,6,7-hexahydronaphthalene (4) and a mechanism is proposed for both microbial and chemical hydroxylation in which the stereochemistry of the product is transition state controlled. The significance of this to the mechanism of microbial C-6β hydroxylation of Δ4-3-ketosteroids is discussed.

Microbial hydroxylation of steroids. 7. Hydroxylation of B-nortestosterone and related compounds by Rhizopus arrhizus ATCC 11145, and 13C nuclear magnetic resonance spectra of some B-norsteroids

1981 ◽  
Vol 59 (11) ◽  
pp. 1651-1655 ◽  
Author(s):  
Herbert L. Holland
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Rhizopus Arrhizus ◽  
Nuclear Magnetic Resonance Spectra ◽  
13C Nuclear Magnetic Resonance ◽  
Mechanism Of Oxidation ◽  
Related Compounds ◽  
Stereoelectronic Interactions ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

The incubation of B-norandrost-4-ene-3-ones and B-nor-3β-hydroxyandrost-5-enes with Rhizopus arrhizus ATCC 11145 has been described. The products are consistent with a mechanism of oxidation at C-6 in which the stereochemistry of substitution at C-6 is controlled by stereoelectronic interactions in the substrate, and is not dictated by enzymic constraint during the reaction. The carbon-13 nuclear magnetic resonance spectra of several B-nor-Δ4 and Δ5 steroids have been presented.

The mechanism of the microbial hydroxylation of steroids. Part 4. The C-6 β hydroxylation of androst-4-ene-3,17-dione and related compounds by Rhizopusarrhizus ATCC 11145

1978 ◽  
Vol 56 (5) ◽  
pp. 694-702 ◽  
Author(s):  
Herbert L. Holland ◽  
Peter R. P. Diakow
Keyword(s):  
Isotope Effect ◽  
Kinetic Isotope Effect ◽  
Enol Form ◽  
Enol Ethers ◽  
Rate Determining Step ◽  
Kinetic Isotope ◽  
Microbial Hydroxylation ◽  
Related Compounds

The steroid analogue 4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone was hydroxylated at C-8α, C-8β, and C-4a by Rhizopusarrhizus. Similar products were obtained by peracid oxidation of the corresponding enol ethers: hydroxylation of estr-4-ene-3,17-dione by the same fungus occurred at the analogous C-6 and C-10 positions. These results are consistent with a mechanism of microbial hydroxylation involving the enol form of the Δ4-3-ketone. Data from the incubations with R. arrhizus of androst-4-ene-3,17-dione specifically labelled with deuterium at C-4, C-6α, or C-6β and from those of other deuterium labelled substrates have been interpreted in terms of a mechanism of C-β hydroxylation involving a rate-determining step before enolization of the ketone, followed by rapid enolization and oxidation of the enol to give the 6β-hydroxy-Δ4-3-ketone. The kinetic isotope effect, kH/kD, for the hydroxylation of androst-4-ene-3,17-dione at C-6β has been found to be 1.2 ± 0.1.

scholarly journals Microbial hydroxylation of novobiocin and related compounds.

1984 ◽  
Vol 37 (2) ◽  
pp. 136-142 ◽  
Author(s):  
O. K. SEBEK ◽  
L. A. DOLAK
Keyword(s):  
Microbial Hydroxylation ◽  
Related Compounds

Zebrafish models for hallucinogenic-related compounds

2013 ◽  
Author(s):  
A. V. Kalueff ◽  
A. M. Stewart ◽  
V. Gjeloshi ◽  
D. Kondaveeti ◽  
N. Neelkantan ◽  
...  
Keyword(s):  
Related Compounds
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