New supramolecular approach for sugar analysis
Başlık çevirisi mevcut değil.
- Tez No: 400314
- Danışmanlar: DR. JUN HU
- Tez Türü: Doktora
- Konular: Kimya, Kimya Mühendisliği, Chemistry, Chemical Engineering
- Anahtar Kelimeler: Belirtilmemiş.
- Yıl: 2006
- Dil: İngilizce
- Üniversite: The University of Akron
- Enstitü: Yurtdışı Enstitü
- Ana Bilim Dalı: Kimya Ana Bilim Dalı
- Bilim Dalı: Belirtilmemiş.
- Sayfa Sayısı: 152
Özet
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Özet (Çeviri)
The main objective of the work presented in this thesis was to develop newmethods for sugar sensing as well as sugar analysis. Boronic acids were chosenas sugar binding motif because of their affinity to sugars. For this purpose anovel type of boronic acid, 3-Pyridinylboronic acid (3pa), was developed. Thisboronic acid was identified as a key sensing element for reversible sugarcomplexation in an aqueous solution at physiological pH. In terms of sugarsensing, 3pba was successfully applied to develop a surface-enhanced Ramanglucose sensor. In this study, indirect detection of glucose was demonstrated forthe first time by using surface-enhanced Raman spectroscopy. Then, takingadvantage of the high binding constant of 3pba with sugars, colorimetricdetections of monosaccharides were done using absorption spectroscopy in thevisible region. The mechanism of the high diol/triol binding of 3pba in a neutralpH was discussed based on the 1H, 13C, and 11B NMR spectroscopic studies.Monosaccharides as well as disaccharides were explored and K constants wereverified by the NMR spectroscopy technique.In terms of sugar analysis, 3pba was used to develop an effective ionizationagent for ESI-MS analysis of sugars. It was demonstrated that the dynamiccovalent supramolecular binding, between the arylboronic acid and sugarsallowed convenient in situ derivatization of the sugar analytes. The zwitterionicnature of 3pba allowed intense ion signals of both the corresponding cations andanions to be observed by a simple switching of the ESI-MS polarity. Isomericmonosaccharides, such as fructose, glucose, and galactose, and isomericdisaccharides, such as lactose and sucrose, were ionized and distinguished by asimple ESI-MS2 experiment. Moreover, zwitterionic aryl boronic acid allowed thefacile formations of structurally well-defined gas phase ions with inert chargesites on trisaccharides. As a consequence, successful demonstration ofsequencing of a trisaccharide was achieved.
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