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Appraisal of an oligomerization behavior of unprotected carbohydrates induced by phosphorus reagent
Authors:Hang Yuan  Xu Yang  Peng Chen  Yan Liu  Guo Tang  Yufen Zhao
Institution:1.Department of Chemical Biology, College of Chemistry and Chemical Engineering, Key Laboratory for Chemical Biology of Fujian Province,Xiamen University,Xiamen,China;2.Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Ministry of Education, Department of Chemistry,Tsinghua University,Beijing,China
Abstract:In this article, a novel oligomerization behavior of unprotected monosaccharides was discovered in a one-pot reaction induced by phosphorus reagent at room temperature. The inherent characteristics of the oligomerization reaction were dissected in detail by mass spectrometry based method combined with NMR technology. It was found that the main glycosidic bonding pattern is (1→6) linkage with 66% regioselectivity for each step. The ratio of α-(1→6) and β-(1→6) glycosidic bonds formed is around 1:1. The reactivity of 1-OH group from aldoses and the driving force from penta-coordinated phosphorus intermediates are the two critical factors for the oligomerization, according to the monitoring experiments by ESI-MS and NMR. Besides, the oligomerization reaction has good compatibility for various aldoses and could expand to O-glycosylated modification of peptides in vitro. The above results will provide a novel enlightenment to develop more convenient and higher-efficient methods for the synthesis of oligosaccharide library.
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