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Structure–Reactivity Relationships in Boronic Acid–Diol Complexation
ACS Omega ( IF 3.7 ) Pub Date : 2018-12-19 00:00:00 , DOI: 10.1021/acsomega.8b02999 William L A Brooks 1 , Christopher C Deng 1 , Brent S Sumerlin 1
ACS Omega ( IF 3.7 ) Pub Date : 2018-12-19 00:00:00 , DOI: 10.1021/acsomega.8b02999 William L A Brooks 1 , Christopher C Deng 1 , Brent S Sumerlin 1
Affiliation
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Boronic acids have found widespread use in the field of biomaterials, primarily through their ability to bind with biologically relevant 1,2- and 1,3-diols, including saccharides and peptidoglycans, or with polyols to prepare hydrogels with dynamic covalent or responsive behavior. Despite a wide range of boronic acid architectures that have been previously considered, there is a need for greater understanding of the structure–reactivity relationships that govern binding affinity to diols. In this study, various boronic acids and other organoboron compounds were investigated to determine their pKa and their binding constants with the biologically relevant diols including sorbitol, fructose, and glucose. Boronic acid pKa values were determined through spectroscopic titration, whereas binding constants were determined by fluorescence spectroscopy during competitive binding studies. Key structure–reactivity relationships clearly indicated that both boronic acid structure and solution pH must be carefully considered. By considering a variety of boronic acids with systematically varied electronics and sterics, these results provide guidance during selection of organoboron compounds in sensing, delivery, and materials chemistry.
中文翻译：
硼酸-二醇络合中的结构-反应性关系
硼酸在生物材料领域有着广泛的用途，主要是因为它们能够与生物相关的1,2-和1,3-二醇（包括糖和肽聚糖）结合，或与多元醇结合以制备具有动态共价或响应行为的水凝胶。尽管之前已经考虑过多种硼酸结构，但仍需要更好地了解控制与二醇的结合亲和力的结构-反应性关系。在这项研究中，研究了各种硼酸和其他有机硼化合物，以确定它们的 pKa及其与生物相关二醇（包括山梨糖醇、果糖和葡萄糖）的结合常数。硼酸pKa值通过光谱滴定测定，而结合常数在竞争性结合研究期间通过荧光光谱测定。关键的结构-反应性关系清楚地表明，必须仔细考虑硼酸结构和溶液 pH 值。通过考虑具有系统变化的电子和空间的各种硼酸，这些结果为传感、传输和材料化学中有机硼化合物的选择提供了指导。
更新日期：2018-12-19
中文翻译：
硼酸-二醇络合中的结构-反应性关系
硼酸在生物材料领域有着广泛的用途，主要是因为它们能够与生物相关的1,2-和1,3-二醇（包括糖和肽聚糖）结合，或与多元醇结合以制备具有动态共价或响应行为的水凝胶。尽管之前已经考虑过多种硼酸结构，但仍需要更好地了解控制与二醇的结合亲和力的结构-反应性关系。在这项研究中，研究了各种硼酸和其他有机硼化合物，以确定它们的 pKa及其与生物相关二醇（包括山梨糖醇、果糖和葡萄糖）的结合常数。硼酸pKa值通过光谱滴定测定，而结合常数在竞争性结合研究期间通过荧光光谱测定。关键的结构-反应性关系清楚地表明，必须仔细考虑硼酸结构和溶液 pH 值。通过考虑具有系统变化的电子和空间的各种硼酸，这些结果为传感、传输和材料化学中有机硼化合物的选择提供了指导。
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