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.
Nicholas
Gillian M
GM
Laboratories of Bioorganic Chemistry and Medicinal Chemistry, NIDDK, National Institutes of Health, Bethesda, Maryland 20892-0820, USA.
Kovác
Pavol
P
Bewley
Carole A
CA
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002942:Circular Dichroism; D003545:Cysteine; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006020:Glycopeptides; D007294:Inositol; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D019086:Bridged Bicyclo Compounds, Heterocyclic; D004187:Disaccharides; D006020:Glycopeptides; D011720:Pyrazoles; D013438:Sulfhydryl Compounds; C021149:bimanes; C089265:mycothiol; D007294:Inositol; D003545:Cysteine