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Martínková, L.; Veselá, A. B., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 1, 279.
N-Unsubstituted 3-oxo amides 5 can be prepared from the corresponding 3-oxo nitriles 4 by using whole cells with nitrile hydratase activity. The amidase activity is suppressed by adding diethyl phosphoramidate (DEPA) to the growth medium.[21] The products are mixtures of the keto and enol form, 5 and 6, respectively (Scheme 3).
Meeeee 8 Meeeeeeeeee ee 8-Mee Meeeee[88]
M8 | M8 | Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|
Me | M | 8.8 eM, 88 eee | 88 | [88] |
8-Mee | M | 8.8 eM, 8 e | 88 | [88] |
8-Mee | M | 8.8 eM, 8 e | 88 | [88] |
8-MeMM8M8 | M | 8.8 eM, 88 eee | 88 | [88] |
8-M8MM8M8 | M | 8.8 eM, 888 eee | 88 | [88] |
8-MeM8M8 | M | 8.8 eM, 88 eee | 88 | [88] |
8-MeM8M8 | M | 8.8 eM, 888 eee | 88 | [88] |
8,8-Me8M8M8 | M | 8.8 eM, 8 e | 88 | [88] |
8-eeeee | M | 8.8 eM, 88 eee | 88 | [88] |
8-eeeee | M | 8.8 eM, 88 eee | 88 | [88] |
8-eeeeeee | M | 8.8 eM, 88 eee | 88 | [88] |
8-eeeeeee | M | 8.8 eM, 8.8 e | 88 | [88] |
M | 8.8 eM, 88 e | 88 | [88] | |
Me | M | 8.8 eM, 88 eee | 88 | [88] |
e-Me | M | 8.8 eM, 88 eee | 88 | [88] |
Me | Me | 8.8 eM, 888 eee | 88 | [88] |
Me | Me | 8.8 eM, 88.8 e | 88 | [88] |
Meeeeeeeeeee Meeeeeeee
8-Mee-8-eeeeeeeeeeeeeeeee (8, M8 = Me; M8 = M); Meeeeee Meeeeeeee:[88]
8-Mee-8-eeeeeeeeeeeeeeeeeeee (8, M8 = Me; M8 = M; 888 ee, 8.88 eeee) eee eeeee ee e eeeeeeeeee ee eeeee eeeee ee Meeeeeeeeee eeeeeeeeeee MMM 88 888 (MM888 = 88.8) ee 8.8 M MM8MM8/M8MMM8 eeeeee (88 eM; eM 8.8) eeeee eeee 8 eM eeeeeee eeeeeeeeeeeeeee [M8MM(M)(MMe)8] (eeeeee M) eee eee eeeeeee eee eeeeeee ee 88 °M eee 8 e. Mee eeeee eeee eeeeeee ee eeeeeeeeeeeeee, eee eee eeeeeeeeee eeeeeeeeee ee eee eeeeeeeeeee eeee MM8Me8 (8 e) eeee eee eeeeeee; eeeee: 888 ee (88%).
Meeeeeeeeeeee, eee eeeeee eee eeeeeeee ee eeeeeeeeee eee eeeeee ee eee eeeeeeeeee (888 eM; MM888 = 8.8) eee eeeeee eee eeeeeeeee ee eeeee eeeee (ee. 888 ee eeee) eeee 8 e (ee eeeee 888 ee, 8.88 eeee); eeeee: 888 ee (88%).
Me eeeeeee eeeeeeeeeeee, 8-eee-8-eeeeeeeeeeeeeeeeeeee (888 ee, 8.88 eeee) ee MeMM (8.8 eM) eee eeeee ee eee eeee eeeeeeeeee (888 eM; MM888 = 8.8) ee eeeeee M eee eeeee eee eeeeeeee eee eeeeeeee (88 eee), eee eeeee eeee eeeeeee ee eeeeeeeeeeeeee eee eeeeeeeeeee ee eeeee eeeeee M (888 eM) eeeeeeeeee eee eeee eeeeee ee eeeeeeeee. Meee eeeeee eeee ee eeeeeee eeeeeeee eeee ee 888 eee eeee eee eeeeeee; eeeee eeeee: 888 ee (88%).
References
[21] | Meeee, M.; Mee, M.; Meeeeee, M. M., Meeeeeeeeee, (8888) 88, 888. |