Polar Hydrophobicity

极性疏水性

• 批准号: 9727176
• 负责人: Stephen DiMagno
• 金额: $ 27.49万
• 依托单位: University of Nebraska-Lincoln
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 1998
• 资助国家: 美国
• 起止时间: 1998-04-15 至 2002-03-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=9727176&HistoricalAwards=false
• 关键词: Polar; Hydrophobicity

With the support of the Organic and Macromolecular Chemistry Program, Profesor Stephen DiMagno, of the Department of Chemistry at the University of Nebraska - Lincoln, is developing `polar hydrophobicity` in the design of fluorinated hosts and guests for molecular recognition. Through the synthesis and study of heavily fluorinated carbohydrate analogs incorporating multiple CF2 (for CHOH) substitutions, Professor DiMagno tests the hypothesis that preorganized sites and bound guests are `harder` than equivalent structures in solution due to the decreased importance of energetic terms arising from electron polarization. The polar hydrophobic effect results from the peculiar physical characteristics of the carbon-fluorine bond, which is at once both extremely polar and hydrophobic. Since the polar characteristics of the C-F bond dominate in crystalline or organized phases while hydrophobic effects are more important in solution, both enthalpic and entropic factors may be more favorable for binding fluorinated analogs than natural substrates. Thus, these studies are expected both to demonstrate the use of polar hydrophobicity as a tool for the design of hosts and guests and to contribute to the general understanding of molecular recognition and hydrogen bonding. The specific recognition and binding of one molecule by another forms the basis of a myriad of chemical and biochemical phenomena. With the support of the Organic and Macromolecular Chemistry Program, Professor Stephen DiMagno, of the Department of Chemistry at the University of Nebraska - Lincoln, is developing the concept of `polar hydrophobicity` in order to design new classes of `hosts` and `guests` for molecular recognition. Professor DiMagno's studies focus on the peculiar physical characteristics of the carbon-fluorine bond, which is at once both extremely polar and highly hydrophobic (water-hating). Through the study of sugar derivatives in which polar and hydrophilic (water-loving) groups are replaced by fluorine atoms, Professor DiMagno obtains information about the roles of polarity and hydrophobic interactions in molecular recognition events, gaining both practical knowledge about the design of new `hosts` and `guests` for general molecular recognition studies as well as detailed information about the biological recognition of natural substrates.

在有机和高分子化学项目的支持下，内布拉斯加大学林肯分校化学系的 Stephen DiMagno 教授正在开发用于分子识别的氟化主体和客体设计中的“极性疏水性”。 通过合成和研究包含多个 CF2（CH3OH）取代的重氟化碳水化合物类似物，DiMagno 教授测试了这样的假设：由于电子产生的能量项的重要性降低，预组织位点和结合客体比溶液中的等效结构“更硬”极化。 极性疏水效应源于碳-氟键的特殊物理特性，它同时具有极强的极性和疏水性。 由于 C-F 键的极性特征在结晶相或有序相中占主导地位，而疏水效应在溶液中更为重要，因此与天然底物相比，焓和熵因子可能更有利于结合氟化类似物。 因此，这些研究有望证明极性疏水性作为设计主体和客体的工具的用途，并有助于对分子识别和氢键的一般理解。 一种分子对另一种分子的特异性识别和结合形成了无数化学和生物化学现象的基础。 在有机和高分子化学项目的支持下，内布拉斯加大学林肯分校化学系的Stephen DiMagno教授正在开发“极性疏水性”的概念，以设计新类别的“主体”和“客体” ` 用于分子识别。 DiMagno 教授的研究重点是碳-氟键的特殊物理特性，该键同时具有极强的极性和高度疏水性（憎水）。 通过研究极性和亲水（亲水）基团被氟原子取代的糖衍生物，DiMagno 教授获得了有关分子识别事件中极性和疏水相互作用的作用的信息，获得了设计新的“用于一般分子识别研究的“主人”和“客人”以及有关天然底物生物识别的详细信息。