Synthesis of the C1-phosphonate analog of UDP-GlcNAc |
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| Authors: | Chang Robert Vo Thanh-Trang Finney Nathaniel S |
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| Affiliation: | Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0358, USA. |
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| Abstract: | We describe the first synthesis of the C1-phosphonate analog of UDP-GlcNAc, based on a new preparation of the corresponding glycosyl phosphonate. This C-glycosyl analog is shown to be a very weak inhibitor (Ki>10 mM) of fungal chitin synthase, indicating that at least in this case the replacement of the anomeric oxygen with a methylene group is not an innocent substitution. |
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| Keywords: | UDP-GlcNAc Glycosyl phosphonate Chitin synthase Glycosyl transferase inhibition |
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