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Preparative scale application of Mucor circinelloides ene-reductase and alcohol dehydrogenase activity for the asymmetric bioreduction of α,β-unsaturated γ-ketophosphonates.
Bioorganic Chemistry ( IF 5.1 ) Pub Date : 2019-12-28 , DOI: 10.1016/j.bioorg.2019.103548
Ignacy Janicki 1 , Piotr Kiełbasiński 1 , Jakub Szeląg 2 , Adrian Głębski 2 , Mirosława Szczęsna-Antczak 2
Affiliation  

The fungus Mucor circinelloides exhibits high potential for green chemistry and technological applications. Recently M. circinelloides, which so far was considered mainly as a platform for biodiesel production, was found to exhibit high ene-reductase activity. In our current research we applied this promising microorganism to the biotransformation of a series of α,β-unsaturated γ-ketophosphonates. The biotransformations were conducted using cheap corn steep liquor or minimal media. The products were obtained with excellent enantiomeric purity (>99% ee in most cases) and in good isolated yields, highlighting the great potential of this microorganism for asymmetric synthesis. Moreover, the products obtained may be further applied as chiral building blocks for the synthesis of biologically active compounds, such as glutamic acid or fosmidomycin derivatives.

中文翻译:

Mucor circinelloides烯还原酶和醇脱氢酶活性的制备规模应用,用于α,β-不饱和γ-酮膦酸酯的不对称生物还原。

真菌Mucor circinelloides具有绿色化学和技术应用的巨大潜力。最近发现,迄今主要被认为是生物柴油生产的平台的环丙旋杆菌(M.circinelloides)表现出高的烯还原酶活性。在我们目前的研究中,我们将这种有前途的微生物应用于一系列α,β-不饱和γ-酮膦酸酯的生物转化。使用廉价的玉米浆或最少的培养基进行生物转化。获得的产物具有优异的对映体纯度(大多数情况下> 99%ee),分离产率也很高,突出了该微生物在不对称合成中的巨大潜力。此外,所得产物还可进一步用作合成生物活性化合物的手性结构单元,
更新日期:2019-12-29
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