   2.5.1.101 | 2,4-diacetamido-2,4,6-trideoxy-alpha-D-mannopyranose + phosphoenolpyruvate + H2O = N,N'-diacetyllegionaminate + phosphate |
C-O bond cleavage process reaction via a oxocarbenium ion intermediate generated by an initial attack of C-3 of phosphoenolpyruvate on the aldehyde of 2,4-diacetamido-2,4,6-trideoxymannose. This attack is facilitated by the divalent cation that serves as an electrophilic catalyst and polarizes the carbonyl of the aldehyde. Water then adds to the oxocarbenium ion intermediate to give a tetrahedral intermediate that subsequently collapses to generate phosphate and the product 2-oxo acid, overview |
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