Total synthesis and proof of structure of mycothiol bimane.

Mycothiol is a low-molecular weight thiol produced by actinomycetes that serves to protect these organisms from oxidative stress and alkylating agents. We report the total synthesis of mycothiol bimane (1) which is a commonly isolated derivative of mycothiol. The synthesis confirms the original structure assignment and unambiguously establishes the absolute stereochemistry of mycothiol to be 1-d-myo-inosityl 2-deoxy-2-(N-acetamido-l-cysteinamido)-alpha-d-glucopyranoside.