Practical, asymmetric synthesis of aromatic-substituted bulky and hydrophobic tryptophan and phenylalanine derivatives

Wei Wang, Chiyi Xiong, Junyi Zhang, Victor J. Hruby

Research output: Contribution to journalArticle

39 Scopus citations

Abstract

Aromatic ring substituted tryptophans and phenylalanines can provide valuable tools in developing highly potent and selective peptide ligands with specific structural features in addition to providing a large lipophilic surface for binding to receptors and for crossing membrane barriers. An efficient method for the synthesis of these novel amino acids has been developed. In the approach, asymmetric hydrogenations of α-enamides using Burk's DuPHOS-based Rh (I) catalysts generated high enantiomerically pure α-amino acid derivatives, which subsequently underwent Suzuki cross couplings with boronic acid derivatives to afford these aromatic substituted amino acids in high yields and high enantioselectivity. The method can allow for the preparation of such amino acids in large scales for extensive structure-activity studies.

Original languageEnglish (US)
Pages (from-to)3101-3110
Number of pages10
JournalTetrahedron
Volume58
Issue number15
DOIs
StatePublished - Apr 8 2002

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Keywords

  • Amino acids
  • Asymmetric hydrogenation
  • DuPHOS
  • Phenylalanine
  • Tryptophan

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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