181506-68-3Relevant academic research and scientific papers
Mapping the pathway toward thiophosphinic pseudopeptides. synthesis of suitably protected PG-Phe-Ψ[P(S)(OX)CH2]-Gly-OY analogues as thiophosphinyl dipeptide isosters (TDI), a comparative study for selective deprotection and further elongation
Vassiliou, Stamatia,Tzouma, Eirini
, p. 10069 - 10076 (2013/11/06)
In the present study, we describe in detail the first synthesis of a new class of phosphorus compounds, thiophosphinyl pseudopeptides. We prepared several fully protected thiophosphinate pseudodipeptides of the general formula PG-Phe-Ψ[P(S)(OX)CH2]-Gly-OY starting from the corresponding phosphinate pseudodipeptide using Lawesson's reagent. Selective deprotection, further elongation, and stability of these compounds were studied, and the results are disclosed. These compounds can be used as transition-state-mimicking inhibitors for several zinc metalloproteases.
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.
