Synthesis of 1-d- and 1-l-myo-inosityl 2-N-acetamido-2-deoxy-α-d-glucopyranoside establishes substrate specificity of the Mycobacterium tuberculosis enzyme AcGI deacetylase Original Research Article

Mycothiol (MSH, 1-d-myo-inosityl 2-(N-acetyl-l-cysteinyl)amido-2-deoxy-α-d-glucopyranoside) is the principal low molecular weight thiol in actinomycetes. The enzyme 1-d-myo-inosityl 2-N-acetamido-2-deoxy-α-d-glucopyranoside deacetylase (AcGI deacetylase) is involved in the biosynthesis of MSH and forms the free amine 1-d-myo-inosityl 2-amino-2-deoxy-α-d-glucopyranoside, which is used in the third of four steps of MSH biosynthesis. Here, we report the synthesis of two isomers of AcGI, which contain either 1-l-myo-inositol or 1-d-myo-inositol. These synthetic products were used to investigate substrate specificity of the Mycobacterium tuberculosis enzyme AcGI deacetylase.