166409-74-1Relevant academic research and scientific papers
Concise and enantioselective synthesis of Fmoc-Pmp(But) 2-OH and design of potent Pmp-containing Grb2-SH2 domain antagonists
Li, Peng,Zhang, Manchao,Peach, Megan L.,Liu, Hongpeng,Yang, Dajun,Roller, Peter P.
, p. 3095 - 3098 (2007/10/03)
(Matrix presented) L-Phosphonomethylphenylalanine (L-Pmp) is an important phosphatase-resistant pTyr analogue. A most concise and stereoselective approach to the synthesis of the suitably protected Fmoc-Pmp(Bu t)2-OH was developed in
New synthesis of D,L-Fmoc protected 4-phosphonomethylphenylalanine derivatives and their enzymatic resolution
Baczko, Krystyna,Liu, Wang-Qing,Roques, Bernard P.,Garbay-Jaureguiberry, Christiane
, p. 2021 - 2030 (2007/10/03)
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.
Enantioselective synthesis of N-Fmoc protected di-tert-butyl 4-phosphonomethyl-L-phenylalanine: A hydrolytically stable analogue of O-phosphotyrosine
Liu,Roques,Garbay-Jaureguiberry
, p. 647 - 650 (2007/10/02)
Fmoc-L-Pmp(tBu)2-OH was prepared with high enantiomeric purity by an asymmetric synthetic pathway, using a camphor sultam as chiral auxiliary.
