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Slomka, C.; Engel, U.; Syldatk, C.; Rudat, J., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 1, 403.
Until 2011, the enantioselective hydrolysis of 6-substituted 5,6-dihydrouracils to their corresponding N-carbamoyl derivatives had not been well studied. However, an investigation of the substrate spectrum of the hydantoinase from Vigna vulgaris showed that it could be utilized for the synthesis of optically pure β-amino acids. d,l-6-Phenyl-5,6-dihydrouracil (d,l-31) is prepared by chemical synthesis as a substrate for the synthesis of l-β-phenylalanine (l-33) (Scheme 25).[159,160]
Meeeee 88 Meeeeeeee ee e,e-8-Meeeee-8,8-eeeeeeeeeeeee[888,888]
Mee eeeeeeeee eeeeeee 8-eeeeeeeeeeeeeee eeeeeeeeeeeee e,e-88 ee eeeeeeeee eeee M-eeeeeeeee-e-β-eeeeeeeeeeeee (e-88) ee eee eeeeeeeeeeee eeee Meeee eeeeeeee; eeeeeeee eeeeeeeeeeeeeeee ee eeee eeeeeeeeeeee eeeee e-β-eeeeeeeeeeeee (e-88) (Meeeee 88).
Meeeee 88 Meeeeeeee ee e-β-Meeeeeeeeeeee eeee e,e-8-Meeeee-8,8-eeeeeeeeeeeee eee M-Meeeeeeee-e-β-eeeeeeeeeeeee Meeee Meeeeeeeeeee eee Meeeeeee Meeeeeeeeeeeeeee[888,888]
Meeee eee eeeeeeeeeeee eeee Meeee eeeeeeee eee eeeeeeeeee ee eee eeeeeeeee eeeeeeeeeeeeeeeee 8-eeeeee-8,8-eeeeeeeeeeeee (e,e-88) eeeee e-88 eeee ee ee 88% ee, eee eeee eeeee eeeeeeee eeeeeeee eeeee eee eeeeeeeeee eeeeeee eeeee 88%. Mee ee eee eeee eeeeeeeeee ee eeeeeee eeeeeeeeeee eeeee eeeeeeeeeeeeeeeeee ee eeeeeeeeee eee eee eeeeeeeee ee β-eeeee eeeee ee eee eeeeeeeeeeee ee 8-eeeeeeeeeee 8,8-eeeeeeeeeeeeeeeeee, eeeee eee eeeeeeeeeeee eeee–eeee eeeeeeeeeee, eeee ee ee eeeeeeee eeee eeeeeeeeee, ee eee eeeeeee ee eeee eeee. Meeeeeee, eee eeeeeee eeeeeeee, eee eeeeeeeeeee ee M-eeeeeeeee-β-eeeeeeeeeeeee, ee eeeeeeeee ee eee eeeeeeeeeeee eee eeeeeee eee eeeeeeee eeeee. Meee eeeeeeee eee eeeee ee ee eeeeee e-eeeeeeeee. M eeeeeee eeeeeeeeeee eeeeeeee ee eeeeeeeeeeeeeeeeee, ee eeeeeeee ee eeeeeeeeee ee eeeee eeeeeeeeee eeeeeeeeee; eeee eee e eeeeee eeeeeeeeee ee eee eM ee eeee ee eee eeeeee eeeeee. Meeeeeeee, eee eeeeeeee ee eeeeeee eee ee eM 8.8 ee Meee eeeeee, eeeee eee eeeeeeeeeeee eeeeee eeeeeee eeeeeeee eeeeee eee eeeeeeeeee ee 8-eeeeee-8,8-eeeeeeeeeeeee (e,e-88).
Me eeeeeeee ee 8-eeeeee-8,8-eeeeeeeeeeeee (e,e-88), eeeee 8-eeeeeeeeeee eeeeeeeeeeeeee 88 eeee eeee eeeeeeee eee eeeeeeee ee eee eeeeeeeee eeeeeeeeeee ee eee Meeee eeeeeeee eeeeeeeeeeee (Meeeee 88).
Meeeee 88 Meeeeeeeee ee Meeeeeeee Meeeeeeeeeeeee Meeee Meeeeeeeeeee eeee Meeee eeeeeeee[888]
| M8 | M8 | M8 | Meeeeeee Meee ee Meeeeeeeee | M Meeeee | Mee |
|---|---|---|---|---|---|
| Me | M | M | 8 | >888 | [888] |
| 8-MM8M8 | M | M | 88 | >888 | [888] |
| 8-MeM8M8 | M | M | –e | >888 | [888] |
| Me | M | M | 88 | 8 | [888] |
| eMe | M | M | 88 | 8 | [888] |
| eMe | M | M | 88 | 8 | [888] |
| Me | M | M | 88 | 8 | [888] |
| Me | Me | M | 8 | – | [888] |
| M | M | Me | 88 | –e | [888] |
e Meeeeeeeee ee eeeeeee-eeeee eeeeee MMMM.
e Mee eeeeeeeeee.
Mee eeeeeeeeee ee 8-eeee-eeeeeeeeeee 8,8-eeeeeeeeeeeeee eeeee eeee eeeeeeeeeeeeeeeeee eeeeee eee e-eeeeeeeeee, eeeeeee eee eeeeeeeeeee ee eeeeeeeeeeeeee eeeeeeeeee ee eeeee eeeee ee M8 eeeeeee ee eeee eeeeeeee eeeee eee eee eeeeeeeeeeeeeeeeee. Me eee eeeeee eeeee ee 8-eeeeee-8,8-eeeeeeeeeeeee (88, M8 = Me; M8 = M8 = M) ee eeeeeeee ee e eeeeee eeeee 88 (M8 = Me; M8 = M8 = M), eee eeeeeeee eeee eeeeeeee eeeeeee, eeeeee ee eeeeeeeeeeeeeeeeee ee eeeeeeeeee. Mee eee ee 8-eeeeeeeeeee eeeeeee ee 8-eeeeeeeeeee 8,8-eeeeeeeeeeeeee eeeeeee ee e eeeee eeee ee eeeeeeeeee eee ee eeeeeeeeee eeeeeeeeeeeeeeeeee.
Meeee eeee eeeeeeee, Meeee eeeeeeee eeeeeeeeeeee eeeeeeeeee 8-eeeeeeeeeee eeeeeeeeeeeeee eeeeeeeeeeeeeeeeee. Meee ee e eeeeeeeee eeeeee eee eee eeeeeeeeee ee eeeeeeeee eeee β-eeeee eeeee eee ee eee eeee eeeeeeee ee MMMM MM. Mee eeeeeee eeeeeee ee eee M-eeeeeeeee eeeee ee eeeeeeeeeeee 88 eeeeeeeeeeeee eee eee eeeeeeeeee, ee eeeeeee eee eeeeeeeeeeeeeeee ee eeeeeeeee eeeeeeeeee. Me eee eeeeeeeeeeeeeee eeeeeeeee ee Meeeeee 8.8.8.8.8.8.8, eee eeeeeeeee ee β-eeeee eeeee ee eeeeeee eee eeeeeeeeee ee eeeeeeeee eeeeeeeee.
Meeeeeeeeeee Meeeeeeee
e,e-8-Meeeee-8,8-eeeeeeeeeeeee (e,e-88); Meeeeee Meeeeeeee:[888,888]
(M)-Meeeeeee eeee (88.8 e, 88.8 eeee) eee eeeee eeee eeee (88.88 e, 888.8 eeee) eee eeeeee ee 888 °M eeee 88 eee, eeeeeeeee ee e eeeeeeeeeee eeeeee eeeeee. Meeee eeeeeeeeee eeeeeeee, eeeeeeeeee eeee (8.88 e, 88.8 eeee) eee eeeee eee eeee eeee ee eeeeeeee eeee. Meeee 8 e, eeeeeee M8M (88 eM) eee eeeee eee eee eeeeeeee eee eeeeee ee 88 °M eee 8 e. Mee eeeeeeee eeeee eee eeeeeeeee eeee eee eeeeeee ee eee eeeeeeeeee. Meeeeeeeeeee, eee eeeeeee eeeeee ee e eeeee eeeeeeeeeee eee eee eeeeeeee ee eeeeeeeeee; eeeee: 88%.
e-β-Meeeeeeeeeeee (e-88); Meeeeee Meeeeeeee Meeee ee Meeeeeee Meeeeeeeeeee eeeeeeee ee Meeeeeee Meeeeeeeeeeeeeee:[888,888]
Mee eeeeeeee eee eeeeeee eee ee 88 °M, eeeee e,e-88 (88 eM) ee 8.8 M Meee eeeeee (eM 8.8; 88 eM) ee eee eeeeeeee ee eee eeeeeeeeeeee eeee Meeee eeeeeeee (888 ee). Me eeeeeeeee eeee MeMM, eee eM ee eee eeeeee eee eeeeeeeeee ee 8.8. Meeee 8 e, e-88 eee eeeeeeeee eeee e-MeMM. Mee eeeeeeeeeeeee ee e-88 eee eeeeeeeeee ee MMMM [eeeeee: Meeee Meeeeeeeeee M Meeeee; eeeeee eeee: 8 µe, 8.8 ee × 888 ee; eeeeee eeeee: 88 eM MM8MMe (eM 8.8)/MeMM (88:88)]; eeeee: 88%; 88% ee. Mee eeeeeeeeee eeeeeeeeeeeeeeee ee e-88 eee eeeeeee eee ee eee eeeeeeee ee MMM8 eee 8–8 e ee 888 °M ee eeeeee e-88; eeeee: 88%.
References
| [159] | MʼMeeee, M.; Meeee, M.; Meeeeeeee, M.; Meeeee, M. M., MMM Meeee., (8888) 8, 8888. |
| [160] | Meeeeeeee, M.; Meeee, M.; Meeeeee, M.; MʼMeeee, M.; Meeeee, M., MM 8 888 888 888, (8888); Meee. Meeee., (8888) 888, 888888. |
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