- N,N'-dialkyldiamide-type phosphate protecting groups for Fmoc synthesis of phosphotyrosine-containing peptides
-
Z-Tyr[P(O)(NHR)2]-OBzl (R=n-Pr and i-Pr) were obtained by reactions of Z-Tyr-OBzl, lithiated with LDA, with N,N -dipropyl- or diisopropyl- phosphorodiamidic chloride. Fmoc derivatives, Fmoc-Tyr][P(O)(NHR)2]-OH, were obtained from them as stable crystals. The P-N bonds are stable toward 20% piperidine in DMF and were cleaved completely with 95% trifluoroacetic acid.
- Ueki, Masaaki,Tachibana, Jun,Ishii, Yusuke,Okumura, Jin,Goto, Mitsutaka
-
-
Read Online
- N,N′-Dialkyldiamide-Type Phosphate Protecting Groups for Fmoc Synthesis of Phosphotyrosine-Containing Peptides: Optimization of the Alkyl Group
-
Synthesis and evaluation of three Fmoc-phosphotyrosine derivatives with a phosphate group protected as N,N'dialkyldiamide (alkyl = Prn, Pri, and Bui) were studied. All the derivatives were obtained as crystals, among which the Bu' derivative (4c) was the best in ease of preparation and excellence in cleavage property. Solid phase synthesis of a methionine-containing peptide, H-TVr(PO3H2)-Val-Pro-Met-Leu-OH, could be done without any problems.
- Ueki, Masaaki,Goto, Mitsutaka,Okumura, Jin,Ishii, Yusuke
-
p. 1887 - 1898
(2007/10/03)
-