当前位置: X-MOL 学术Mar. Biotechnol. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Synthesis of Knoevenagel Adducts Under Microwave Irradiation and Biocatalytic Ene-Reduction by the Marine-Derived Fungus Cladosporium sp. CBMAI 1237 for the Production of 2-Cyano-3-Phenylpropanamide Derivatives.
Marine Biotechnology ( IF 3 ) Pub Date : 2020-03-03 , DOI: 10.1007/s10126-020-09953-8
Willian Garcia Birolli 1, 2 , Lucas Lima Zanin 1 , David Esteban Quintero Jimenez 3 , André Luiz Meleiro Porto 1
Affiliation  

The organic synthesis has been driven by the need of sustainable processes, which also requires efficiency and cost-effectiveness. In this work, we described the synthesis of nine Knoevenagel adducts between cyanoacetamide and aromatic aldehydes ((E)-2-cyano-3-(phenyl)acrylamide derivatives), employing triethylamine as catalyst under microwave irradiation in 30 min with excellent yields (93–99% yield). Then, these adducts were employed in the C–C double bond bioreduction by the marine-derived fungus Cladosporium sp. CBMAI 1237 for obtention of 2-cyano-3-phenylpropanamide derivatives in mild conditions and short reaction time for a whole-cells reduction (phosphate buffer pH 7.0, 32 °C, 130 rpm, 8 h) with good yields (48–90%). It is important to emphasize that the experimental conditions, especially the reaction time, should be carefully evaluated for the obtention of high yields. Since a biodegradation process consumed the obtained product in extended periods, probably due to the use of the substrate as carbon and nitrogen source. This approach showed that the use of coupled and greener catalysis methods such as microwave irradiation and biocatalytic reduction, which employs unique biocatalysts like marine-derived fungi, can be an interesting tool for the obtention of organic molecules.

中文翻译:

海洋衍生真菌Cladosporium sp。在微波辐射下合成Knoevenagel加合物和生物催化还原烯。用于制备2-氰基-3-苯基丙酰胺衍生物的CBMAI 1237。

有机合成是由可持续过程的需求驱动的,这也需要效率和成本效益。在这项工作中,我们描述了氰基乙酰胺和芳香醛((E)-2-氰基-3-(苯基)丙烯酰胺衍生物)之间九种Knoevenagel加合物的合成,在微波辐射下以三乙胺为催化剂在30分钟内以优异的收率(93 –99%的收益)。然后,这些加合物被海洋真菌Cladosporium用于CC双键生物还原。sp。CBMAI 1237可在温和条件下获得2-氰基-3-苯基丙酰胺衍生物,且反应时间短,可减少全细胞(磷酸盐缓冲液pH 7.0、32°C,130 rpm,8 h),收率良好(48–90% )。必须强调的是,应仔细评估实验条件,特别是反应时间,以确保获得高收率。由于生物降解过程会长时间消耗获得的产物,这可能是由于将底物用作碳和氮源。这种方法表明,使用诸如海洋辐射真菌等独特的生物催化剂的微波辐射和生物催化还原等耦合且绿色的催化方法可能是获得有机分子的有趣工具。
更新日期:2020-03-03
down
wechat
bug