Synthesis and conformational features of topographically constrained designer chimeric amino adds: The β-isopropyl phenylalanines

Subo Liao, Mark D. Shenderovich, Jun Lin, Victor J. Hruby

Research output: Contribution to journalArticle

28 Scopus citations

Abstract

All four optically pure isomers of the highly conformationally constrained novel chimeric amino acid, β-isopropylphenylalanine or β- phenylleucine, were asymmetrically synthesized in five to six steps in 20 - 25% overall yield. Computer-assisted molecular modeling revealed that the β- isopropyl group in these chimeric amino acids plays the dominant role in determining the most favorable side chain conformations.

Original languageEnglish (US)
Pages (from-to)16645-16662
Number of pages18
JournalTetrahedron
Volume53
Issue number49
DOIs
StatePublished - Dec 8 1997

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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