Microbial hydroxylation of acronycine

1974 ◽  
Vol 17 (6) ◽  
pp. 653-654 ◽  
Author(s):  
D. R. Brannon ◽  
D. R. Horton ◽  
Gordon H. Svoboda



2003 ◽  
Vol 222 (2) ◽  
pp. 183-186 ◽  
Author(s):  
Mohammad Ali Faramarzi ◽  
Mojtaba Tabatabaei Yazdi ◽  
Mohsen Amini ◽  
Gholamreza Zarrini ◽  
Abbas Shafiee


1975 ◽  
Vol 53 (14) ◽  
pp. 2041-2044 ◽  
Author(s):  
Herbert L. Holland ◽  
Barbara J. Auret

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.



1979 ◽  
Vol 57 (13) ◽  
pp. 1585-1587 ◽  
Author(s):  
Herbert L. Holland ◽  
Peter R. P. Diakow

The products arising from the incubations of C-6α and C-6β chloro-, fluoro-, and methyl-substituted Δ4-3-keto steroids with the C-6β hydroxylating fungus Rhizopusarrhizus ATCC 11145 have been identified, and their formation rationalised in terms of Δ3,5 enolic intermediates. The incubations of C-6 chloro and methyl Δ3,5 enol acetates with R. arrhizus, and the oxidations by m-chloroperoxybenzoic acid of the corresponding enol ethyl ethers have also been described. The relevance of the results so obtained to the mechanism of C-6β hydroxylation of Δ4-3-keto steroids by R. arrhizus is discussed.



1985 ◽  
Vol 63 (5) ◽  
pp. 1127-1131 ◽  
Author(s):  
Herbert L. Holland ◽  
P. Chinna Chenchaiah

The testosterone derivatives A-nortestosterone acetate and B-homo-Δ1-testosterone acetate have been incubated with Rhizopusarrhizus, a fungus which hydroxylates testosterone at the C-6β and C-11 α positions. These modes of hydroxylation were also observed for the A-nor steroid. The B-homo steroid, however, was oxidized at C-2β and concurrently hydroxylated at C-6β and C-7aβ (but not at C-11) by R. arrhizus. Δ1 steroids of conventional skeleton were hydroxylated at C-11α by R. arrhizus; in addition, Δ1-androstenedione was epoxidized at the 1,2β position. No C-6 hydroxylation of conventional Δ1,4-3-ketosteroids was observed.



1995 ◽  
Vol 6 (1) ◽  
pp. 7-14 ◽  
Author(s):  
Steffen Breiter ◽  
Dietmar Schlosser ◽  
Dieter Weiss ◽  
Hans-Peter Schmauder


1964 ◽  
Vol 29 (6) ◽  
pp. 1333-1336 ◽  
Author(s):  
Allen I. Laskin ◽  
Paul Grabowich ◽  
Barbara Junta ◽  
Carol de Lisle Meyers ◽  
Josef Fried


2001 ◽  
Vol 11 (4-6) ◽  
pp. 361-366 ◽  
Author(s):  
A. de Raadt ◽  
S. Feichtenhofer ◽  
H. Griengl ◽  
M.F. Klingler ◽  
H. Weber




1998 ◽  
Vol 39 (11) ◽  
pp. 1309-1312 ◽  
Author(s):  
Horacio F. Olivo ◽  
Michael S. Hemenway ◽  
Mikail H. Gezginci


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