STUDIES RELATED TO CHORISMIC ACID

与分支酸相关的研究

• 批准号: 3276373
• 负责人: PAUL A BARTLETT
• 金额: $ 12.06万
• 依托单位: UNIVERSITY OF CALIFORNIA BERKELEY
• 依托单位国家: 美国
• 财政年份: 1983
• 资助国家: 美国
• 起止时间: 1983-03-01 至 1986-02-28
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/3276373
• 关键词: antibiotics; chemical synthesis; cyclic compound; drug design /synthesis /production; shikimate; stereochemistry

We propose a number of synthetic and mechanistic studies related to chorismic acid, a key intermediate in the biosynthesis of aromatic metabolites. 1. We plan to elucidate the stereochemistry of the Claisen rearrangement of chorismate to prephenate by developing a synthesis of stereospecifically labeled deuterochorismate. 2. We will synthesize a transition state analog of the rearrangement and evaluate it as an inhibitor of chorismate mutase enzymes and as a potential antibiotic. 3. We will develop total syntheses of the still-virgin intermediates in the shikimic acid pathway: shikimate-3-phosphate, 5-enolpyruvylshikimate-3-phosphate, and chorismate itself.

我们提出了一些与以下相关的综合性和机械性研究 芳香族生物合成的关键中间体--分枝酸 代谢物。1.我们计划阐明Claisen的立体化学 通过开发一种合成分支酸来重排预苯酸酯 立体专一性标记的次甲基色水杨酸。2.我们将合成一个 重排的过渡态模拟，并将其作为 分支酸变位酶抑制剂，并作为潜在的抗生素。3. 我们将开发全合成的仍然处女的中间体在 莽草酸途径：莽草酸-3-磷酸， 5-烯丙酮基莽草酸-3-磷酸和分支酸本身。