Abstract

The chemical synthesis of α-d-Glc p-(1 → 2)- α-d-Glc p-(1 → 3)- α-d-Glc p-O-(CH 2) 8COOCH 3 ( 9), a substrate specific for α-glucosidase I, is reported. This enzyme removes the terminal α-d-Glc p unit to produce α-d-Glc p-(1 → 3)- α-d-Glc p-O-(CH 2) 8COOCH 3 ( 10). This is the first synthetic substrate described for glucosidase I that allows kinetic evaluation of substrates and inhibitors of this enzyme. Tetramethylrhodamine was coupled to 9 through an ethylenediamine linker to produce a brilliant red derivative. Addition of this fluorescent dye did not affect enzyme binding to the substrate, as determined by a comparison of the K m value (1.3 mM). The fluorescent label allows visual detection of 2–3 pmol of product by TLC.

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