Enantioselective ene‐reduction of E‐2‐cyano‐3‐(furan‐2‐yl) acrylamide by marine and terrestrial fungi and absolute configuration of (R)‐2‐cyano‐3‐(furan‐2‐yl) propanamide determined by calculations of electronic circular dichroism (ECD) spectra
This work reports the green organic chemistry synthesis of E‐2‐cyano‐3(furan‐2‐yl) acrylamide under microwave radiation (55 W), as well as the use of filamentous marine and terrestrial‐derived fungi, in the first ene‐reduction of 2‐cyano‐3‐(furan‐2‐yl) acrylamide to (R)‐2‐cyano‐3‐(furan‐2‐yl)propana...
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| Published in: | Chirality (New York, N.Y.) Vol. 31; no. 7; pp. 534 - 542 |
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| Abstract | This work reports the green organic chemistry synthesis of E‐2‐cyano‐3(furan‐2‐yl) acrylamide under microwave radiation (55 W), as well as the use of filamentous marine and terrestrial‐derived fungi, in the first ene‐reduction of 2‐cyano‐3‐(furan‐2‐yl) acrylamide to (R)‐2‐cyano‐3‐(furan‐2‐yl)propanamide. The fungal strains screened included Penicillium citrinum CBMAI 1186, Trichoderma sp. CBMAI 932 and Aspergillus sydowii CBMAI 935, and the filamentous terrestrial fungi Aspergillus sp. FPZSP 146 and Aspergillus sp. FPZSP 152. A compound with an uncommon CN‐bearing stereogenic center at the α‐C position was obtained by enantioselective reactions mediated in the presence of the microorganisms yielding the (R)‐2‐cyano‐3‐(furan‐2‐yl) propanamide 3a. Its isolated yield and e.e. ranged from 86% to 98% and 39% to 99%, respectively. The absolute configuration of the biotransformation products was determined by time‐dependent density functional theory (TD‐DFT) calculations of electronic circular dichroism (ECD) spectra. Finally, the tautomerization of 2‐cyano‐3‐(furan‐2‐yl) propanamide 3a to form an achiral ketenimine was observed and investigated in presence of protic solvents. |
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| AbstractList | This work reports the green organic chemistry synthesis of E‐2‐cyano‐3(furan‐2‐yl) acrylamide under microwave radiation (55 W), as well as the use of filamentous marine and terrestrial‐derived fungi, in the first ene‐reduction of 2‐cyano‐3‐(furan‐2‐yl) acrylamide to (R)‐2‐cyano‐3‐(furan‐2‐yl)propanamide. The fungal strains screened included Penicillium citrinum CBMAI 1186, Trichoderma sp. CBMAI 932 and Aspergillus sydowii CBMAI 935, and the filamentous terrestrial fungi Aspergillus sp. FPZSP 146 and Aspergillus sp. FPZSP 152. A compound with an uncommon CN‐bearing stereogenic center at the α‐C position was obtained by enantioselective reactions mediated in the presence of the microorganisms yielding the (R)‐2‐cyano‐3‐(furan‐2‐yl) propanamide 3a. Its isolated yield and e.e. ranged from 86% to 98% and 39% to 99%, respectively. The absolute configuration of the biotransformation products was determined by time‐dependent density functional theory (TD‐DFT) calculations of electronic circular dichroism (ECD) spectra. Finally, the tautomerization of 2‐cyano‐3‐(furan‐2‐yl) propanamide 3a to form an achiral ketenimine was observed and investigated in presence of protic solvents. This work reports the green organic chemistry synthesis of E-2-cyano-3(furan-2-yl) acrylamide under microwave radiation (55 W), as well as the use of filamentous marine and terrestrial-derived fungi, in the first ene-reduction of 2-cyano-3-(furan-2-yl) acrylamide to (R)-2-cyano-3-(furan-2-yl)propanamide. The fungal strains screened included Penicillium citrinum CBMAI 1186, Trichoderma sp. CBMAI 932 and Aspergillus sydowii CBMAI 935, and the filamentous terrestrial fungi Aspergillus sp. FPZSP 146 and Aspergillus sp. FPZSP 152. A compound with an uncommon CN-bearing stereogenic center at the α-C position was obtained by enantioselective reactions mediated in the presence of the microorganisms yielding the (R)-2-cyano-3-(furan-2-yl) propanamide 3a. Its isolated yield and e.e. ranged from 86% to 98% and 39% to 99%, respectively. The absolute configuration of the biotransformation products was determined by time-dependent density functional theory (TD-DFT) calculations of electronic circular dichroism (ECD) spectra. Finally, the tautomerization of 2-cyano-3-(furan-2-yl) propanamide 3a to form an achiral ketenimine was observed and investigated in presence of protic solvents. This work reports the green organic chemistry synthesis of E ‐2‐cyano‐3(furan‐2‐yl) acrylamide under microwave radiation (55 W), as well as the use of filamentous marine and terrestrial‐derived fungi, in the first ene‐reduction of 2‐cyano‐3‐(furan‐2‐yl) acrylamide to (R)‐2‐cyano‐3‐(furan‐2‐yl)propanamide. The fungal strains screened included Penicillium citrinum CBMAI 1186, Trichoderma sp. CBMAI 932 and Aspergillus sydowii CBMAI 935, and the filamentous terrestrial fungi Aspergillus sp. FPZSP 146 and Aspergillus sp. FPZSP 152. A compound with an uncommon CN‐bearing stereogenic center at the α‐C position was obtained by enantioselective reactions mediated in the presence of the microorganisms yielding the ( R )‐2‐cyano‐3‐(furan‐2‐yl) propanamide 3a . Its isolated yield and e.e. ranged from 86% to 98% and 39% to 99%, respectively. The absolute configuration of the biotransformation products was determined by time‐dependent density functional theory (TD‐DFT) calculations of electronic circular dichroism (ECD) spectra. Finally, the tautomerization of 2‐cyano‐3‐(furan‐2‐yl) propanamide 3a to form an achiral ketenimine was observed and investigated in presence of protic solvents. |
| Author | Vasconcellos, Suzan P. Santos, Fernando M. Barreiro, Juliana C. Jimenez, David E.Q. Porto, André L.M. Batista, João M. |
| Author_xml | – sequence: 1 givenname: David E.Q. surname: Jimenez fullname: Jimenez, David E.Q. organization: Instituto de Química de São Carlos, Universidade de São Paulo ‐ USP – sequence: 2 givenname: Juliana C. orcidid: 0000-0002-3657-2620 surname: Barreiro fullname: Barreiro, Juliana C. email: juliana.barreiro@gmail.com organization: Instituto de Química de São Carlos, Universidade de São Paulo ‐ USP – sequence: 3 givenname: Fernando M. surname: Santos fullname: Santos, Fernando M. organization: Instituto de Química, Universidade Federal Fluminense – sequence: 4 givenname: Suzan P. surname: Vasconcellos fullname: Vasconcellos, Suzan P. organization: Universidade Federal de São Paulo‐UNIFESP – sequence: 5 givenname: André L.M. surname: Porto fullname: Porto, André L.M. organization: Instituto de Química de São Carlos, Universidade de São Paulo ‐ USP – sequence: 6 givenname: João M. orcidid: 0000-0002-0267-2631 surname: Batista fullname: Batista, João M. organization: Universidade Federal de São Paulo‐UNIFESP |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31197903$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1016/j.cbpa.2005.01.001 10.1002/ejoc.200300513 10.1007/s10529-009-0037-y 10.1002/anie.199505211 10.1016/j.copbio.2004.06.011 10.1016/j.tetlet.2014.07.032 10.1246/cl.2000.998 10.1039/b822048b 10.1002/anie.201302195 10.1016/j.ejmech.2009.04.017 10.1038/35051706 10.1007/s10126-012-9464-1 10.1016/j.bcab.2015.03.005 10.2174/2211544711302010009 10.1016/S1367-5931(98)80041-0 10.1016/j.bcab.2015.03.001 10.1007/12_2010_86 10.1139/v62-352 10.1016/j.tet.2016.02.014 10.1016/j.tet.2009.11.065 10.1016/j.tet.2012.05.092 10.1039/c0gc00877j 10.1016/0040-4020(73)80245-5 10.1016/j.molcatb.2015.01.017 10.1038/35051736 10.1016/S0076-6879(97)86021-1 10.1039/CS9972600463 10.1016/S1367-5931(98)80040-9 10.1039/C4RA06619G 10.1021/op990101l |
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| Keywords | enoate reductase electronic circular dichroism marine- and terrestrial-derived fungi Knoevenagel condensation biocatalysis |
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| Snippet | This work reports the green organic chemistry synthesis of E‐2‐cyano‐3(furan‐2‐yl) acrylamide under microwave radiation (55 W), as well as the use of... This work reports the green organic chemistry synthesis of E-2-cyano-3(furan-2-yl) acrylamide under microwave radiation (55 W), as well as the use of... This work reports the green organic chemistry synthesis of E ‐2‐cyano‐3(furan‐2‐yl) acrylamide under microwave radiation (55 W), as well as the use of... This work reports the green organic chemistry synthesis of E‐2‐cyano‐3(furan‐2‐yl) acrylamide under microwave radiation (55 W), as well as the use of... |
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| SubjectTerms | Absolute configuration Acrylamide Aspergillus biocatalysis Biotransformation Chemical synthesis Circular dichroism Configurations Density functional theory Dichroism electronic circular dichroism Enantiomers enoate reductase Fungi Knoevenagel condensation marine‐ and terrestrial‐derived fungi Mathematical analysis Microorganisms Microwave radiation Microwaves Organic chemistry Penicillium citrinum Reduction Terrestrial environments Time dependence |
| Title | Enantioselective ene‐reduction of E‐2‐cyano‐3‐(furan‐2‐yl) acrylamide by marine and terrestrial fungi and absolute configuration of (R)‐2‐cyano‐3‐(furan‐2‐yl) propanamide determined by calculations of electronic circular dichroism (ECD) spectra |
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