181506-69-4Relevant articles and documents
Synthesis and comparative study on the reactivity of peptidyl-type phosphinic esters: Intramolecular effects the alkaline and acidic cleavage of methyl β-carboxyphosphinates
Georgiadis,Dive,Yiotakis
, p. 6604 - 6610 (2001)
Using the phosphinic analogue of Cbz-Phe-Gly-OEt 1a as a template for this study, several phosphinic esters (2a-g) were prepared, employing an efficient method for each case. The activity of these derivatives under conventional deprotection conditions was studied, and the results are listed comparatively. The effect of steric hindrance as well as the contribution of neighboring groups in the rate of hydrolysis of suitably selected β-carboxyphosphinates under acidic and deprotection conditions was examined. The results clearly demonstrate that a significant acceleration of phosphinate cleavage occurs due to the intermediacy of a five-membered, mixed anhydride-type species. This was supported by the observation that similar interactions were not observed in the case of hindered α-carboxyphosphinate homologous derivatives.
The synthesis of phosphinic acid based proteinase inhibitors
Hamilton, Robert,Wharry, Scott,Walker, Brian,Walker, Brian J.
, p. 761 - 764 (1999)
The phenyl phosphinate analogues of valine and phenylalanine with extended chains at phosphorus have been prepared as racemic mixtures and also in high optical purity. Kinetic data clearly indicate specific inhibitory activity for analogues having (R) configuration at α-carbon. A similar synthetic approach provides a simplified route to reported C2 symmetrical HIV inhibitors.
Protection of the hydroxyphosphinyl function of phosphinic dipeptides by adamantyl. Application to the solid-phase synthesis of phosphinic peptides
Yiotakis, Athanasios,Vassiliou, Stamatia,Jiracek, Jiri,Dive, Vincent
, p. 6601 - 6605 (2007/10/03)
To develop solid-phase synthesis of phosphinic peptides, different FmocXaaΦ{PO(OAd)CH2}XaaOH building blocks have been prepared, where Fmoc is (fluorenylmethoxy)carbonyl. In this respect, the protection of the hydroxyphosphinyl function in these phosphinic dipeptides by the adamantyl group turns out to be convenient. The phosphinic adamantyl esters are completely stable in basic conditions and can be removed under relatively mild acidic conditions. Using these building blocks, despite the bulkiness of the adamantyl group, no particular problem of coupling was observed during the solid-phase synthesis of phosphinic peptides by the Fmoc strategy. The developed methodology is of particular interest to facilitate the development of potent inhibitors of zinc-metalloproteases.
