Bioorganic & medicinal chemistry letters

Development of l-3-aminotyrosine suitably protected for the synthesis of a novel nonphosphorylated hexapeptide with low-nanomolar Grb2-SH2 domain-binding …

YL Song, PP Roller, YQ Long

Index: Song, Yan-Li; Roller, Peter P.; Long, Ya-Qiu Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 12 p. 3205 - 3208

Full Text: HTML

Citation Number: 15

Abstract

Synthesis of orthogonally protected (2S)-2-amino-3-(3-amino-4-hydroxy-phenyl)-propionic acid (10) suitable for solid phase peptide synthesis and its first use for the preparation of nonphosphorylated Grb2-SH2 domain antagonists (4a–c) are reported. The 3-aminotyrosine containing sulfoxide-cyclized hexapeptide (4b) exhibited potent Grb2-SH2 domain binding affinity with IC50= 50nM, which represents the highest affinity yet reported for a peptide ...