K. Baczko, Wang Liu, B. Roques
Feb 5, 1996
Citations
0
Influential Citations
12
Citations
Journal
Tetrahedron
Abstract
Abstract A new synthesis of N -Fmoc 4-phosphonomethyl-D,L-phenylalanine protected under di- tert - butyl or dimethyl phosphonate forms (Fmoc-Pmp(OR) 2 ), suitable for solid phase peptide synthesis is described. Resolution of these hydrolytically stable analogs of O -phosphotyrosine was tried either by fractional recrystallization of diastereoisomeric salts or by using the subtilisin Carlsberg esterase. Only the enzymatic resolution of ethyl 4-[(dimethylphosphono)methyl]-D,L-phenylalaninate succeeded. These results are discussed by comparison with the literature data. The L and D amino acids were used to prepare separately, through solid-phase peptide synthesis, followed by deprotection of dimethylphosphonate group by trimethylsilyliodide (TMSI) in acetonitrile, the L and D isomers of Glu-Asp-Val- Pmp -Glu-Asn-Leu-His-Thr, a peptide corresponding to a potentially phosphorylated site of the phosphatase PTP 1C.