期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 18, 页码 10798-10804出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01519
关键词
-
资金
- National Institutes of Health (NIH) [R01AI130684]
Streptococcus pneumoniae sialidase SpNanB is an intramolecular trans-sialidase (IT-sialidase) and a virulence factor that is essential for streptococcal infection of the upper and lower respiratory tract. SpNanB catalyzes the formation of 2,7-anhydro-N-acetylneuraminic acid (2,7-anhydro-NeuSAc), a potential prebiotic that can be used as the sole carbon source of a common human gut commensal anaerobic bacterium. We report here the development of an efficient one-pot multi enzyme (OPME) system for synthesizing 2,7-anhydro-NeuSAc and its derivatives. Based on a crystal structure analysis, an N-cyclohexyl derivative of 2,7-anhydro-neuraminic acid was designed, synthesized, and shown to be a selective inhibitor against SpNanB and another Streptococcus pneumoniae sialidase SpNanC. This study demonstrates a new strategy of synthesizing 2,7anhydro-sialic acids in a gram scale and the potential application of their derivatives as selective sialidase inhibitors.
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