1121707-28-5Relevant articles and documents
Synthesis of the phosphinic analogue of thyrotropin releasing hormone
Matziari, Magdalini,Bauer, Karl,Dive, Vincent,Yiotakis, Athanasios
, p. 8591 - 8593 (2008)
(Chemical Equation Presented) The synthesis of the phosphinic analogue of thyrotropin releasing hormone (TRH) GlpΨ[P(O)(OH)]HisProNH2, where the scissile peptide bond of TRH has been replaced by the hydrolytically stable phosphinic bond, has been achieved by a multistep synthetic strategy, providing thus one of the most potent synthetic inhibitors of pyroglutamyl peptidase II (PPII) reported to date (170 nM). The key synthetic step, an Ugi-type condensation reaction, produced directly the suitably protected for solid-phase peptide synthesis pseudodipeptidic block FmocGlu(OMe)Ψ[P(O)(OH)] His(Tr)OH. Formation of the pyroglutamic ring was performed on solid phase, providing thus a general method for synthesizing pyroglutamyl phosphinic peptides on solid phase. Using this strategy, the phosphinic analogue of TRH has been synthesized for the first time.
