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    • 109. 发明授权
    • Process for preparing optically active hydantoins
    • 制备光学活性乙内酰脲的方法
    • US4812406A
    • 1989-03-14
    • US775090
    • 1985-09-12
    • Satomi TakahashiYukio YamadaYasuyoshi UedaYasuhiro KatayamaYoshio ShimadaKiyoshi Watanabe
    • Satomi TakahashiYukio YamadaYasuyoshi UedaYasuhiro KatayamaYoshio ShimadaKiyoshi Watanabe
    • C07D233/72C07D233/74C07D311/68C07D317/60C07D405/06C07D491/10C12P17/02C12P17/10C12P17/18C12P41/00C12R1/01C12R1/07C12R1/15C12R1/365C12P13/04
    • C07D405/06C07D233/74C07D311/68C07D317/60C07D491/10C12P17/02C12P17/10C12P17/18C12P41/009
    • A process for preparing optically active hydantoins having the general formula (II): ##STR1## wherein R.sup.1 and R.sup.2, which are different from each other, are independently alkyl group, aralkyl group, aryl group, substituted alkyl group, substituted aralkyl group, or substituted aryl group, or R.sup.1 and R.sup.2 form an asymmetric cyclic compound, characterized in that one configuration of racemic N-carbamoyl-.alpha.-amino acid having the general formula (I): ##STR2## wherein R.sup.1 and R.sup.2 are as above, is enzymatically converted into the corresponding hydantoins.The present invention provides a process for an optical resolution with a high efficiency which can be used for the synthesis of (S)-6-fluoro-spiro-[chroman-4,4'-imidazolidine]-2',5'-dione (USAN; Sorbinil), which is an optically active hydrantoins attracting public attention as a preventive or a remedy for the particular chronic symptoms of diabetes such as cataract and neuropathy, and (S)-.alpha.-methyl-3,4-dihydroxyphenylalanine (L-methyldopa), which is an optically active amino acid widely used as antihypertensives. Further, the present invention provides a novel finding that N-carbamoyl-.alpha.-amino acid having no hydrogen atom on its .alpha.-carbon atom can be biochemically converted into hydantoins by an enzymatic cyclization reaction.
    • 制备具有通式(II)的光学活性乙内酰脲的方法:其中R1和R2彼此不同,其独立地为烷基,芳烷基,芳基,取代的烷基,取代的芳烷基 基团或取代的芳基,或R 1和R 2形成不对称环状化合物,其特征在于具有通式(I)的外消旋N-氨基甲酰基-α-氨基酸的一种构型:其中R1和R2 如上所述,被酶转化成相应的乙内酰脲。 本发明提供了可用于(S)-6-氟 - 螺 - [苯并二氢吡喃-4,4'-咪唑烷] -2',5'-二酮的合成的高效光学拆分方法。 (USAN; Sorbinil)是一种光学活性的水解素,引起公众的注意,作为预防或治疗糖尿病的特殊慢性症状如白内障和神经病,以及(S)-α-甲基-3,4-二羟基苯丙氨酸(L 甲基多巴),其是广泛用作抗高血压药物的光学活性氨基酸。 此外,本发明提供了一种新的发现,其α-碳原子上不具有氢原子的N-氨基甲酰基-α-氨基酸可以通过酶环化反应生物化学转化成乙内酰脲。