Design and synthesis of novel χ2-constrained phenylalanine, naphthylalanine, and tryptophan analogues and their use in biologically active melanotropin peptides

Wei Wang, Minying Cai, Chiyi Xiong, Junyi Zhang, Dev Trivedi, Victor J. Hruby

Research output: Contribution to journalArticle

41 Scopus citations

Abstract

A series of novel hydrophobic, bulky χ2-constrained phenylalanine, naphthylalanine, and tryptophan derivatives was designed and synthesized. The key steps involved asymmetric hydrogenations of α-enamides using Burk's DuPHOS-based Rh(I) catalysts to give high enantiomerically pure α-amino acid derivatives. The subsequent Suzuki cross couplings of the amino acid analogues with boronic acid derivatives afforded these aromatic substituted amino acids in high yields and with high enantioselectivity. The incorporation of these novel χ2-constrained amino acids into peptides and peptidomimetics provides fruitful information in the development of peptide and peptidomimetic ligands of melanotropins and an understanding of the interactions between ligands and receptors/acceptors.

Original languageEnglish (US)
Pages (from-to)7365-7374
Number of pages10
JournalTetrahedron
Volume58
Issue number36
DOIs
StatePublished - Sep 2 2002

Keywords

  • Asymmetric hydrogenation
  • Constrained amino acids
  • DuPHOS
  • Naphthylalanine
  • Phenylalanine
  • Tryptophan

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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