Total synthesis of the methanogenic cofactors methanofuran and methanofuran b

Article abstract of DOI:10.1021/ja00068a022

Methanofuran, 3-[p-((N-(N″-((4R,5S)- or (4S,5A)-4,5,7-tricarboxyheptanoyl)-γL-glutamyl-γ-L-glutamyl)-β- amino)ethyl]phenoxymethyl}-5-(aminomethyl)furan, and methanofuran b, 3-{p-[(N-(-γ-L-glutamyl-γ-L-glutamyl-γ-L-glutamyl-γ-L- glutamyl)-β-amino)ethyl]phenoxymethyl}-5-(aminomethyl)furan, are the first cofactors involved in the conversion of carbon dioxide to methane by the methanogenic bacteria Methanobacterium thermoautotrophicum and Methanosarcina barkeri, respectively. These two cofactors have now been synthesized, starting from glutamic acid, dimethyl glutarate, methyl 5-formyl-3-furoate, and tyramine. The synthetic compounds give the same NMR and mass spectra and biological activities as the natural cofactors.