Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 8, Pages 5339-5357Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00184
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Funding
- Ministry of Science and Technology (Taiwan) [MOST 109-0210-01-18-02, MOST 107-2113-M-001-030-, MOST 105-2113-M-001-012-MY2]
- Academia Sinica [AS-SUMMIT-109]
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This study describes a double one-pot strategy for the synthesis of N-glycans, assisted by an IM-MS analysis approach for rapid screening of optimized glycosylation reaction conditions. The method enables the efficient synthesis of high-mannose type N-glycans with excellent stereo- and regioselectivities.
N-Glycans are major constituents of several cellular glycoproteins. One-pot strategies for the synthesis ofN-glycans arecrucial for the rapid generation of pure samples to determine theirbiological functions. Herein, we describe a double one-pot strategyfor the synthesis ofN-glycans assisted by an IM-MS analysisapproach for rapid screening of optimized glycosylation reactionconditions. This research includes triflate-mediated direct beta-mannosylation and tandem glycosylation in a one-pot strategy forthe synthesis of the challengingN-linked trisaccharide core beta-5.Furthermore, a one-pot sequential glycosylation of theN-linkedtrisaccharide core7furnishes diverse high-mannose typeN-glycanswith excellent stereo- and regioselectivities. In particular, ionmobility-mass spectrometry-based quantitative analysis is appliedto identify the stereo- and regioselective outcomes of the crude reaction mixtures to develop a highly efficient one-pot protocol.
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