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.

摘要：研究人员表示，他最近 开发了一种简单的环状二肽， Strecker合成非蛋白原性α-氨基酸 以苯甲醛、氨和HCN为原料， 非常高的对映体过量，该提案详细说明了 他的工作的扩展，旨在发展一种通用的方法。 对于α-氨基酸及其衍生物的不对称合成， 以及那些旨在增加对 催化作用的机制和负责物种的真实性质 用于催化。据指出， 这些建议是： A.生物活性化合物芳基甘氨酸衍生物的不对称合成 重要性 B。α-氨基水解的替代方法探索 腈转化为α-氨基酸。 C.进一步探索允许的底物范围。 D. Ugi和Passerini的不对称版本的开发 反应. E.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。