Total synthesis and proof of structure of mycothiol bimane |
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| Authors: | Nicholas Gillian M Kovác Pavol Bewley Carole A |
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| Institution: | Laboratories of Bioorganic Chemistry and Medicinal Chemistry, NIDDK, National Institutes of Health, Bethesda, Maryland 20892-0820, USA. |
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| Abstract: | 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. |
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