Asymmetric synthesis of boc-N-methyl-p-benzoyl-phenylalanine. Preparation of a photoreactive antagonist of substance P

Article abstract of DOI:10.1016/S0960-894X(98)00219-4

The asymmetric synthesis of (S)-Boc-N-methyl-p-benzoyl-phenylalanine was performed by alkylation of sultam Boc-sarcosinate. The levorotatory sultam led to (S)-Boc-N-methyl amino acids with high optical purity. This photoreactive amino acid was incorporated into the sequence of a Substance P peptide antagonist. Comparison of the affinity and antagonistic properties of Biotinyl-apa-[D-Pro⁹, MePhe(pBz)¹⁰, Trp¹¹]SP for human tachykinin NK-1 receptor demonstrated that this photoreactive antagonist should be a suitable tool for photolabelling studies.