Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 22, Pages 6618-6621Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201501890
Keywords
glycosylation; gold; nucleosides; total synthesis; tunicamycin
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Funding
- National Natural Science Foundation of China [21372253, 21432012]
- Ministry of Science and Technology of China [2012ZX09502-002]
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The tunicamycins constitute a delicate mimic of the bisubstrate intermediates of N-acetyl-D-hexosamine-1-phosphate translocases and thus inhibit bacterial cell-wall synthesis and the Nglycosylation of eukaryotic proteins. An efficient approach to the synthesis of this unique type of nucleoside antibiotics is now reported and features the assembly of five modules in a highly stereoselective and robust manner. A Mukaiyama aldol reaction, intramolecular acetal formation, gold(I)-catalyzed O and Nglycosylation, and final Nacylation were used as the key steps.
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