STEREOCONTROLLED AMINE AND PEPTIDE ANALOG SYNTHESIS

立体控制胺和肽模拟合成

• 批准号: 3288276
• 负责人: PAUL B HOPKINS
• 金额: $ 10.14万
• 依托单位: UNIVERSITY OF WASHINGTON
• 依托单位国家: 美国
• 财政年份: 1986
• 资助国家: 美国
• 起止时间: 1986-08-01 至 1989-07-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/3288276
• 关键词: alkenes; allyl compound; amines; chemical structure function; chemical synthesis; drug design /synthesis /production; drug screening /evaluation; peptides; selenium; stereochemistry; synthetic vaccines

1. A synthetically practical, single-step procedure for the conversion of allylic selenides to protected allylic amines has been developed. The reaction has been shown to be useful for the preparation of optically active allylic amines. The proposed research seeks to develop a version of this reaction which utilizes a chiral auxiliary for the more convenient, general preparation of optically active allylic amines. Intramolecular variations and a modification for the formation of carbon-carbon bonds are proposed. II. Peptide mimics are of significant utility in bioorganic chemistry. The proposed research seeks to complete the first fully stereocontrolled approach to alkene isosteres of dipeptides, and incorporate these into an analog of the immunodominant site of influenza virus hemagluttin. These analogs will be compared to the native substances as antigens and immunogens. Similarly, several isoteric mimics for a Beta-bend are proposed. These compounds will likewise be synthesized and immunologically tested.

1.一种综合实用的单步程序，用于转换 从烯丙基硒到受保护的烯丙基胺已被开发出来。这个 反应已被证明对制备光学材料是有用的 活性烯丙基胺。这项拟议的研究旨在开发一种版本的 该反应利用了手性助剂， 光学活性烯丙基胺的一般制备。分子内 用于形成碳-碳键的变体和修饰是 建议。 多肽模拟物在生物有机化学中具有重要的应用价值。这个 拟议的研究试图完成第一个完全定型控制的研究 探讨二肽的烯烃等位体，并将其合并到一个 流感病毒血凝素免疫优势部位的类似物。这些 类似物将作为抗原和天然物质进行比较 免疫原。类似地，Beta折弯的几个等轴线模拟 建议。这些化合物将同样被合成并免疫 测试过。

项目成果

A qualitative fluorescence-based assay for tyrosyl radical scavenging activity: ovothiol A is an efficient scavenger.

基于荧光的定性测定酪氨酰自由基清除活性：卵硫醇 A 是一种有效的清除剂。

• DOI: 10.1016/0003-2697(89)90440-5
• 发表时间: 1989
• 期刊: Analytical biochemistry
• 影响因子: 2.9
• 作者: Holler,TP;Hopkins,PB
• 通讯作者: Hopkins,PB

Sequence preferences of DNA interstrand cross-linking agents: dG-to-dG cross-linking at 5'-CG by structurally simplified analogues of mitomycin C.

DNA 链间交联剂的序列偏好：通过结构简化的丝裂霉素 C 类似物在 5-CG 处进行 dG 到 dG 交联。

• DOI: 10.1021/bi00491a017
• 发表时间: 1990
• 期刊: Biochemistry
• 影响因子: 2.9
• 作者: Weidner,MF;Sigurdsson,ST;Hopkins,PB
• 通讯作者: Hopkins,PB

Site-specific metal-induced damage of mitomycin C-crosslinked DNA fragments in the presence of sodium dithionite.

在连二亚硫酸钠存在的情况下，丝裂霉素 C 交联 DNA 片段的位点特异性金属诱导损伤。

• DOI: 10.1016/0027-5107(93)90103-m
• 发表时间: 1993
• 期刊: Mutation research
• 作者: Millard,JT;Hopkins,PB
• 通讯作者: Hopkins,PB