A. Paquet, M. Johns
Jan 12, 2009
Citations
0
Influential Citations
25
Citations
Journal
International journal of peptide and protein research
Abstract
The protected oligophosphoseryl peptides from bovine caseins, Z-Xxx-(Ser[PO(OPh)2])3-Glu(OBzl)-OBzl for Xxx = Ile, Val, Gly, Leu and Ph = phenyl, were synthesized in high yields by stepwise lengthening using Boc-Ser[PO(OPh)2]-OH as acylating carboxyl component and N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride as coupling reagent. The hydrogenolytic deprotection (PtO2) was carried out with the valine derivative and with the tetrapeptide Ser[PO(OPh)2]3-Glu(OBz)-OBzl. Phosphorylation of oligoseryl peptides failed to give the expected products. Large scale phosphorylation of protected serine was carried out in the presence of triethylamine using absolute ether as a solvent. 2,2,2-Trichloroethyl group (Tc) was shown to be a useful phosphorus protecting moiety in phosphopeptide synthesis: Boc-Ser[PO(OTc)2]-OBzl, Z-Ser[PO(OTc)2]-OBzl and Boc-Glu(OBzl)-Ser[PO(OTc)2]-OBzl were synthesized in high yields using bis-(2,2,2-trichloroethyl) phosphochloridate.