Abstract
The asymmetric synthesis of novel, potent phosphoramidate alpha(2-6)sialyltransferase transition-state analogue inhibitors such as (R)-9 (K(i)=68 microM) is described, via condensation of cytidine phosphitamide 6 with key chiral, non-racemic alpha-aminophosphonates, prepared in >98% ee by Mitsunobu azidation followed by Staudinger reduction of the corresponding chiral, non-racemic alpha-hydroxyphosphonates.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amides / chemical synthesis*
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Amides / pharmacology
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / pharmacology
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Phosphoric Acids / chemical synthesis*
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Phosphoric Acids / pharmacology
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Sialyltransferases / chemical synthesis*
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Sialyltransferases / pharmacology
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Stereoisomerism
Substances
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Amides
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Enzyme Inhibitors
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Phosphoric Acids
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phosphoramidic acid
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Sialyltransferases