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The affects of the 5-thiomannosides (1–3) can be replicated by their common intermediate—5-thiomannose (4). (A) A proposed hydrolysis reaction for 1 proceeds through an iminium intermediate to yield 5-thiomannose which may possibly become activated as the poor mannosyltransferase substrate GDP-5-thiomannose. (B) 5-thiomannose replicates the affects of 1 on SKI-1 N-glycosylation and zymogen activation while a more hydrolase resistant analogue does not.
