ASYMMETRIC CATALYSIS OF STRECKER AMINO ACID SYNTHESIS

STRECKER 氨基酸合成的不对称催化

• 批准号: 6019082
• 负责人: MARK A LIPTON
• 金额: $ 4.98万
• 依托单位: PURDUE UNIVERSITY
• 依托单位国家: 美国
• 财政年份: 1995
• 资助国家: 美国
• 起止时间: 1995-08-01 至 2000-07-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/6019082
• 关键词: aminoacid; catalyst; chemical structure; chemical synthesis; cyclic peptides; dipeptides; glycine; stereochemistry

DESCRIPTION: The principal investigator states that he has recently developed a simple, cyclic dipeptide which effectively catalyzes the Strecker synthesis of the non-proteinogenic alpha-amino acid phenylglycine from benzaldehyde, ammonia and HCN in high yield and extraordinarily high enantiomeric excess and that this proposal details extensions to his work directed at the development of a general method for the asymmetric synthesis of alpha-amino acids and their derivatives, as well as those directed toward an increased understanding of the mechanism of catalysis and the true nature of the species responsible for catalysis. It is indicated that the specific targets detailed in this proposal are: A. Asymmetric synthesis of arylglycine derivatives of biological importance. B. Exploration of alternate methods for the hydrolysis of alpha-amino nitriles to alpha-amino acids. C. Further exploring the scope of substrates allowed. D. Development of asymmetric versions of the Ugi and Passerini reactions. E. Modified catalysts for the synthesis of aliphatic alpha-amino acids. F. Obtaining detailed structural information on the catalytic complex.

描述：首席研究员表示，他最近 开发了一种简单的环状二肽，可有效催化 Strecker 合成非蛋白α-氨基酸 以苯甲醛、氨和 HCN 为原料，高产率地生产苯基甘氨酸 极高的对映体过量，该提案详细说明了 他的工作的扩展旨在开发通用方法 用于α-氨基酸及其衍生物的不对称合成， 以及那些旨在加深对 催化机制和负责物种的真实性质 用于催化。据悉，具体目标详见 该提案是： A. 生物芳基甘氨酸衍生物的不对称合成 重要性。 B. α-氨基水解替代方法的探索 腈转化为α-氨基酸。 C.进一步探索允许的基材范围。 D. Ugi 和 Passerini 的非对称版本的开发 反应。 E.用于合成脂肪族α-氨基酸的改性催化剂。 F. 获得催化复合物的详细结构信息。