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.

在有机和大​​分子化学计划的支持下，内布拉斯加州大学化学系 - 林肯大学的化学系教授史蒂芬·迪马格诺（Stephen DiMagno）正在设计“极性疏水性宿主”和嘉宾的“极性疏水性”。 通过合成和研究，含有多个CF2（用于CHOH）取代的重氟化碳水化合物类似物，Dimagno教授检验了以下假设：由于在电力偏振中产生的能量术语的重要性，因此，预组织地点和有限的宾客“比溶液中的等效结构都比解决方案更难。 极性疏水作用是由碳氟键的特殊物理特征引起的，碳氟键立即极极性和疏水性。 由于C-F键的极性特征在晶体或有组织的相中占主导地位，而疏水作用在溶液中更为重要，因此，焓和熵因素都比天然底物更有利地有利于结合氟化的类似物。 因此，预计这些研究都可以证明使用极性疏水性作为设计宿主和客人的工具，并有助于对分子识别和氢键的一般理解。 另一个分子对一个分子的特定识别和结合形成了无数化学和生化现象的基础。 在有机和大​​分子化学计划的支持下，内布拉斯加州大学林肯大学化学系的斯蒂芬·迪马格诺（Stephen Dimagno）教授正在开发“极性疏水性”的概念，以设计新的宿主和``宿主''和``客人''的概念。 Dimagno教授的研究集中于碳氟键的独特物理特征，该碳键立即极性和高度疏水（讨厌水）。 通过研究糖衍生物的研究，其中极性和亲水性（热爱水）被氟原子取代，Dimagno教授获得了有关极性和疏水相互作用在分子识别事件中的作用的信息，从而获得了有关新宿主的指定和``宿主''events''events of Moleculac识别研究的实际知识。