engleski

Synthesis, intramolecular migrations and enzymic hydrolysis of partially pivaloylated methyl alpha-D-mannopyranosides

A series of methyl O-pivaloyl-alpha-D- mannopyranosides was synthesized using pivaloyl chloride in pyridine. The 3, 6-di-O-pivaloyl derivative 6 undergoes intramolecular transesterification in neutral conditions (buffer, pH 7.2) to give its 2, 6-di-O-pivaloyl analogue 5. The course of its migration was followed using 14C-labelled 6. As opposed to 6 compound 5 was shown to be a good substrate for esterases present in rabbit serum. Thus, regioselective enzymic hydrolysis led to the preferential cleavage of the 2-OPiv group to yield a mixture of 2- and 6-O-monopivalates in ratio 1:2.6.

methyl alpha-D-mannopyranosides ; acylated ; Esterases ; Rabbit serum ; Enzymic hydrolysis ; Pivaloyl migrations

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