- Effective multi-step functional biotransformations of steroids by a newly isolated Fusarium oxysporum SC1301
-
A fungus Fusarium oxysporum SC1301 was isolated from soil samples, which could transform androst-4-ene-3,17-dione, androst-1,4-diene-3,17-dione, dehydroepiandrosterone, progesterone, testosterone, and pregnenolone to give testolactone in 76-98% yields. Especially, for progesterone and pregnenolone, multi-step functional transformations, including oxygenative esterification of 20-ketosteroids, hydrolysis of ester, oxidation of C-17 OH group, oxygenative lactonization of 17-ketosteroids, 1-dehydrogenation, oxidation of C-3 OH group and Δ5→4 CC bond migration, could proceed effectively to yield testolactone as a single product. This is the first example that a F. oxysporum species shows catalytic capability of ring-D lactonization. The results are remarkably distinguished from those previously reported for the closely-related fungus F. oxysporum var. cubense, which predominantly mediates the hydroxylations at different positions of steroids. In addition, F. oxysporum SC1301 may serve as a valuable biocatalyst for the production of testolactone.
- Zhang, Hongliu,Ren, Jie,Wang, Yu,Sheng, Cuo,Wu, Qiaqing,Diao, Aipo,Zhu, Dunming
-
-
Read Online
- Phytosterols as precursors for the synthesis of aromatase inhibitors: Hemisynthesis of testololactone and testolactone
-
Using β-sitosterol and stigmasterol as precursor materials, a concise and efficient hemisynthesis of aromatase inhibitors: testololactone and testolactone was accomplished in a well-established reaction scheme. It involves highly effective Oppaneur oxidation of both β-sitosterol as well as stigmasterol to generate the required enone moiety in ring 'A' of the desired steroid system. The Oppaneur oxidation products of both β-sitosterol and stigmasterol were then subjected to oxidative cleavage of the side chain to produce 4-androstene-3,17-dione. Baeyer-Villiger oxidation of 4-androstene-3,17-dione using m-CPBA yielded testololactone. Dehydrogenation of 4-androstene-3,17-dione using phenylselenyl chloride in ethyl acetate followed by selenoxide elimination with H2O2 in dichloromethane furnished androstenedienone. Baeyer-Villiger oxidation of the resulting androstenedienone yielded the desired testolactone (overall yield 33%). This expeditious reaction scheme may be exploited for the bulk production of aromatase inhibitors (especially testolactone marketed under the brand name Teslac) from the most abundant and naturally occurring phytosterols like β-sitosterol.
- Lone, Shabir H.,Bhat, Khursheed A.
-
p. 164 - 168
(2015/03/04)
-
- Steroids' transformations in Penicillium notatum culture
-
The application of Penicillium notatum genus for biotransformations of steroids has been investigated. The reactions observed include insertion of an oxygen atom into D-ring of steroids, 15α-hydroxylation of 17α-methyl testosterone derivatives, ester bond hydrolysis, and degradation of a testosterone derivatives side chain. Microbial production of testolactones, the biologically active compounds, was also achieved using this strain in up to 98% yield.
- Bartmanska, Agnieszka,Dmochowska-Gladysz, Jadwiga,Huszcza, Ewa
-
p. 193 - 198
(2007/10/03)
-
- Δ1 Dehydrogenation of corticoids without side chain degradation by Septomyxa
-
This invention discloses an improved biotransformation process for the introduction of a double bond between carbon atoms 1 and 2 in corticoids by Septomyxa without degradation of the corticoid side chain.
- -
-
-