600708-96-1Relevant articles and documents
Synthesis of a new conformation-constrained L-tyrosine analogue as a potential scaffold for SH2 domain ligands
Liu, Fa,Zha, Hui-Yan,Yao, Zhu-Jun
, p. 6679 - 6684 (2007/10/03)
The enantioselective synthesis of a new tricyclic tyrosine analogue is reported. This conformation-contrained SH2 domain ligand scaffold 2 was designed on the basis of the natural ligand, whose structure contains the elements of a tyrosine moiety having χ1 and χ2 angles constrained to values observed for a phosphotyrosyl (pTyr) residue bound to the p56lck SH2 domain. It represents a unique, highly constrained amino acid, which may be of value in signal transduction studies. Three key steps, an asymmetric tandem Michael addition, an intramolecular Friedel-Crafts reaction, and an intramolecular Mannich reaction, were successfully applied in the presented synthetic route.