- Development of a high-yielding bioprocess for 11-α hydroxylation of canrenone under conditions of oxygen-enriched air supply
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A high yielding bioprocess for 11-α hydroxylation of canrenone (1a) using Aspergillus ochraceus ATCC 18500 was developed. The optimization of the biotransformation involved both fermentation (for achieving highly active mycelium of A. ochraceus) and biotransformation with the aim to obtain 11-α hydroxylation with high selectivity and yield. A medium based on sucrose as C-source resulted particularly suitable for conversion of canrenone into the corresponding 11-hydroxy derivative, whereas the use of O2-enriched air and dimethyl sulfoxide (DMSO) as a co-solvent for increasing substrate solubility played a crucial role for obtaining high yields (>95%) of the desired product in high chemical purity starting from 30?mM (10.2?g/L) of substrate. The structure of the hydroxylated product was confirmed by a combination of two-dimensional NMR proton-proton correlation techniques.
- Contente, Martina Letizia,Guidi, Benedetta,Serra, Immacolata,De Vitis, Valerio,Romano, Diego,Pinto, Andrea,Lenna, Roberto,de Souza Oliveira, Ricardo Pinheiro,Molinari, Francesco
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Read Online
- Structural characterization of 1β,11α-dihydroxycanrenone biotrans-formed from canrenone by Aspergillus ochraceus SIT34205
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Canrenone (1) was biotransformed into 11α-hydroxycanrenone (2) and a main byproduct (3) by Aspergillus ochraceus SIT34205. Compound 3 was separated and purified using silica gel column chromatography, and its structure was characterized via MS and NMR methods. These results indicated that 3 was 1β,11α-dihydroxycanrenone and the product of further hydroxylation of 2. Thus, investigating the structure and synthesis of 3 may be a promising method to improve the efficiency and purity of 2.
- Rong, Shao Feng,Zhang, Xiao Li,Ding, Bao Mei,Wang, Yi Fei,Pan, Xian Hua,Zhang, Jian,Shen, Yi
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experimental part
p. 313 - 316
(2012/05/05)
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- Processes for preparation of 3-keto-7alpha-alkoxycarbonyl-delta-4,5- steroids and intermediates useful therein
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Multiple novel reaction schemes, novel process steps and novel intermediates are provided for the synthesis of epoxymexrenone and other compounds of Formula I wherein:-A-A- represents the group -CHR4-CHR5- or -CR4=CR5- R3, R4 and R5 are independently selected from the group consisting of hydrogen, halo, hydroxy, lower alkyl, lower alkoxy, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, cyano, varyloxy;R1 represents an alpha-oriented lower alkoxycarbonyl or hydroxyalkyl radical;-B-B- represents the group -CHR6-CHR7- or an alpha- or beta- oriented group: where R6 and R7 are independently selected from the group consisting of hydrogen, halo, lower alkoxy, acyl, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, alkyl, alkoxycarbonyl, acyloxyalkyl, cyano and aryloxy; andR8 and R9 are independently selected from the group consisting of hydrogen, hydroxy, halo, lower alkoxy, acyl, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, alkyl, alkoxycarbonyl, acyloxyalkyl, cyano and aryloxy, or R8 and R9 together comprise a carbocyclic or heterocyclic ring structure, or R8 or R9 together with R6 or R7 comprise a carbocyclic or heterocyclic ring structure fused to the pentacyclic D ring.
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