N,N′-Dialkyldiamide-Type Phosphate Protecting Groups for Fmoc Synthesis of Phosphotyrosine-Containing Peptides: Optimization of the Alkyl Group

Article abstract of DOI:10.1246/bcsj.71.1887

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.