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

  • Bioorg Med Chem Lett. 1998 Jun 2;8(11):1369-74. doi: 10.1016/s0960-894x(98)00219-4.
P Karoyan  1 ,  S Sagan ,  G Clodic ,  S Lavielle ,  G Chassaing
Affiliations
  • 1. Laboratoire de Chimie Organique Biologique associé au CNRS, Université P. et M. Curie, UMR 7613, Paris, France.
PMID: 9871768 DOI: 10.1016/s0960-894x(98)00219-4
Abstract

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.