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β-(3-吡啶基)-DL-α-丙氨酸的合成改进及拆分

Improved synthesis and resolution of beta-(3-pyridyl)-DL-alpha-alanine.

作者信息

Folkers K, Kubiak T, Stepinski J

出版信息

Int J Pept Protein Res. 1984 Sep;24(3):197-200. doi: 10.1111/j.1399-3011.1984.tb00947.x.

DOI:10.1111/j.1399-3011.1984.tb00947.x
PMID:6500805
Abstract

beta-Benzamido-alpha-(3-pyridyl)-DL-alpha-alanine hydrochloride was synthesized from 3-pyridinecarboxyaldehyde via the azlactone which was hydrolyzed to the acrylic acid before hydrogenation. The methyl ester was effectively resolved with subtilisin. The optical purity of the D-isomer was established, since the D-isomer was used in synthesis of antagonists of the luteinizing hormone releasing hormone.

摘要

β-苯甲酰胺基-α-(3-吡啶基)-DL-α-丙氨酸盐酸盐由3-吡啶甲醛经乙内酰脲合成，乙内酰脲在氢化前水解为丙烯酸。甲酯用枯草杆菌蛋白酶有效拆分。由于D-异构体用于合成促黄体生成激素释放激素拮抗剂，因此确定了其光学纯度。

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