Exploiting an aromatic aglycone as a reporter of glycosylation stereochemistry in the synthesis of 1,6-linked maltooligosaccharides |
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| Institution: | 1. Centre for Carbohydrate Chemistry, School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich NR4 7TJ, UK;2. Department of Biological Chemistry, John Innes Centre, Norwich NR4 7UH, UK;1. Renewable Product Technology Research Unit, National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, 1815 N. University St., Peoria, IL 61604, USA;2. Crop Bioprotection Research Unit, National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, 1815 N. University St., Peoria, IL 61604, USA;1. Department of Food Science & Biotechnology, College of BioNano Technology, Gachon University, Seongnam, Republic of Korea;2. Department of Food Science & Technology, BK21+ Project Team, and Carbohydrate Bioproduct Research Center, Sejong University, Seoul, Republic of Korea;3. Department of Radiology and Imaging Sciences, Indiana University, School of Medicine, Indianapolis, IN, USA;4. Graduate School of Biotechnology, and Institute of Life Science and Resources, Kyung Hee University, Yongin, Republic of Korea;5. Whistler Center for Carbohydrate Research and Department of Food Science, Purdue University, West Lafayette, IN, USA;1. “Petru Poni” Institute of Macromolecular Chemistry, 41A Grigore Ghica Voda Alley, 700487 Iasi, Romania;2. Department of Microbiology, Faculty of Biology, University of Barcelona, Av. Diagonal 643, 08028 Barcelona, Spain;3. University of Maribor, Institute of Engineering Materials and Design, Smetanova ulica 17, 2000 Maribor, Slovenia |
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| Abstract: | Analysis of glycosylation stereoselectivity in the synthesis of branched maltooligosaccharides is hampered by poor spectral dispersion due to the repetitive nature of the saccharide chain and overlap of sugar H-1 signals with benzylic proton signals from the typically used benzyl ether protecting groups. A suitably protected p-methoxyphenyl maltoside acceptor, when coupled with benzylated maltooligosaccharide donors, gives discrete aglycone 1H NMR signals that can be used to report on the stereoselectivity of 1,6-glycosylation reactions. |
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