Figure 1
General reaction mechanism of inverting glycoside hydrolases. The upper part shows the proposed conformational changes of the sugar in subsite −1 (G−1). β-4C1, 2,5B and α-4C1 are the conformations of G−1 in the substrate, oxocarbenium ion intermediate (transition state) and product, respectively. 2SO and 5S1 are the conformations of the other intermediates. The lower part shows the proposed catalytic process of GH8 enzymes. The reaction follows the single-displacement mechanism through the oxocarbenium ion intermediate. The numbers in the left part represent the order of the displacement reaction, i.e. protonation of the glycosidic bond occurs followed by nucleophilic attack of an activated water molecule. G−1 is shown as a six-membered sugar. The substrate, transition intermediate and product are shown in the left, middle and right panels, respectively. Before and after forming the oxocarbenium intermediate, G−1 forms 2SO and 5S1 conformations, respectively. |