Convenient solid-phase synthesis of oligopeptides using pentacoordinated phosphoranes with amino acid residue as building blocks.
The reactive intermediates of pentacoordinated phosphoranes with amino acids (P(5)-AA) as building blocks, which were obtained by the reaction of O-phenylene phosphorochloridate with N,O-bis(trimethylsilyl)amino acids, were linked to a solid-phase support containing a hydroxymethyl polystyrene functional group. The first amino acid residue was coupled to the solid-phase support after washing the resin with organic solvent. Repeating the procedure led to oligopeptides linked on the resin. A series of free oligopeptides including tetra-Gly, di-Val, tri-Val, di-Leu, di-Phe, and Phe-Leu were obtained after cleavage from solid-phase support. The structure of these oligopeptides were determined by IR, (1)H NMR, FAB-MS, and HPLC.
Li
Zhaolong
Z
Key Laboratory of Bioorganic Phosphorus Chemistry, Ministry of Education, Department of Chemistry, School of Life Sciences and Engineering, Tsinghua University, Beijing 100084, PR China. zhlli@tsinghua.edu.cn
Fu
Hua
H
Gong
Hegui
H
Zhao
Yufen
Y
D000596:Amino Acids / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D008956:Models, Chemical; D009842:Oligopeptides / Q000032:analysis / Q000138:chemical synthesis*; D010753:Phosphoranes / Q000737:chemistry*; D010756:Phosphoric Acids / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D014297:Trimethylsilyl Compounds / Q000737:chemistry
D000596:Amino Acids; D009842:Oligopeptides; D010753:Phosphoranes; D010756:Phosphoric Acids; D014297:Trimethylsilyl Compounds