Abstract

In this study, we developed a method for the production of androsta-9(11)-diene-3,17-dione (Δ⁹⁽¹¹⁾-AD), which is a combination of phytosterol side-chain microbial oxidation with simultaneous 9α‑hydroxylation and subsequent chemical regio-selective dehydration of 9α-hydroxy-3,17-diketo-intermediate without isolation and purification. Phytosterol was converted into 9α-hydroxyandrost-4-ene-3,17-dione (9-OH-AD) with the use of the wild-type Mycobacterium sp. VKM Ac-1817D strain. The product was extracted from the culture medium with the use of an organic solvent and dehydrated in the extract with mineral acid. The resulting Δ⁹⁽¹¹⁾-AD was purified with the selective crystallization method. Minor products were isolated and identified. It has been shown that this strain is capable of sterol transformation with the formation of methyl ester of 9α-hydroxypregn-4-ene-3-one-20-carboxylic acid. Our approach makes it possible to simplify the flow chart for production of the target compound. It not only eliminates 9-OH-AD loss but also minimizes the amount of production waste.

中文翻译：

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大豆植物甾醇转化为Androsta-4,9（11）-diene-3,17-dione

摘要

在这项研究中，我们开发了一种生产雄激素9（11）-二烯-3,17-二酮（Δ9 ^（11） -AD）的方法，该方法是植物甾醇侧链微生物氧化与9α同时发生的组合-羟基化和随后的9α-羟基-3,17-二酮中间产物的化学区域选择性脱水，无需分离和纯化。利用野生型分枝杆菌属（Mycobacterium sp。）将植物甾醇转化成9α-羟基雄烷-4-烯-3,17-二酮（9-OH-AD）。VKM Ac-1817D菌株。使用有机溶剂从培养基中提取产物，并在提取物中用无机酸脱水。所得的Δ9 ^（11）用选择性结晶法纯化-AD。分离并鉴定了次要产物。已经显示出该菌株能够通过形成9α-羟基孕烯-4-烯-3-一-20羧酸的甲酯来固醇转化。我们的方法可以简化目标化合物生产的流程图。它不仅消除了9-OH-AD的损失，而且还最大程度地减少了生产浪费。