title: Asymmetric synthesis of Boc-N-methyl-p-benzoyl-phenylalanine. Preparation of a photoreactive antagonist of substance P.
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.
authors.affiliation: Laboratoire de Chimie Organique Biologique associé au CNRS, Université P. et M. Curie, UMR 7613, Paris, France.
authors.forename: P
authors.initials: P
authors.lastname: Karoyan
authors.forename: S
authors.initials: S
authors.lastname: Sagan
authors.forename: G
authors.initials: G
authors.lastname: Clodic
authors.forename: S
authors.initials: S
authors.lastname: Lavielle
authors.forename: G
authors.initials: G
authors.lastname: Chassaing
mesh_terms: D000478:Alkylation; D000818:Animals; D001710:Biotin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D016466:CHO Cells; D006224:Cricetinae; D000242:Cyclic AMP / Q000378:metabolism; D006801:Humans; D008968:Molecular Conformation; D064729:Neurokinin-1 Receptor Antagonists; D010649:Phenylalanine / Q000138:chemical synthesis*; D010777:Photochemistry; D018041:Receptors, Neurokinin-2 / Q000378:metabolism; D013329:Structure-Activity Relationship; D013373:Substance P / Q000031:analogs & derivatives / Q000037:antagonists & inhibitors* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: C117558:N-(tert-butoxycarbonyl)-N-methyl-4-benzoylphenylalanine; D064729:Neurokinin-1 Receptor Antagonists; D018041:Receptors, Neurokinin-2; C117612:substance P, biotinyl-apa-Pro(9)-MePhe(pBz)(10)-Trp(11)-; D013373:Substance P; D010649:Phenylalanine; D001710:Biotin; D000242:Cyclic AMP