Synthesis of a new tyrosine analogue having χ_1 and χ_2 angles constrained to values observed for an SH2 domain-bound phosphotyrosyl residue

摘要

Synthesis is reported of a new tricyclic amino acid, (±)-(rel-2S,3R)-2-carboxy-1,2,3,4,5,6-hexahydro- 8-hydroxy-1,5-methano-3-methyl-3-benzazocine (2), which contains within its structure the elements of a tyrosine moiety having χ_1 and χ_2 angles (168°and -95°, respectively) constrained to values observed for a phosphotyrosyl (pTyr) residue bound to the 56~ick SH2 domain (χ_1 and χ_2 values of 163°and -94°, respectively). Additionally, the φ angle of N-acylated 2 correlates well with the φ angle of the SH2 domain-bound pTyr residue.