First total synthesis of redox coenzyme factor 420

Abstract

The first total synthesis of Methanobacterium redox coenzyme Factor 420 (F420) has been achieved by the formation of a phosphotriester bond between a protected 10-D-ribityl-8-hydroxy-5-deazaisoalloxazine moiety and a peptide moiety, (L-lactate-γ-L-glutamyl)-L-glutamic acid tribenzyl ester, by the phosphite triester approach using β,β,β-trichloroethyl phosphorodichloridite, followed by successive deprotection.