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 Citations (Scopus)

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
StatePublished - Dec 8 1997

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Phenylalanine
Molecular Computers
Amino Acids
Molecular modeling
Isomers
Conformations

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis and conformational features of topographically constrained designer chimeric amino adds : The β-isopropyl phenylalanines. / Liao, Subo; Shenderovich, Mark D.; Lin, Jun; Hruby, Victor J.

In: Tetrahedron, Vol. 53, No. 49, 08.12.1997, p. 16645-16662.

Research output: Contribution to journalArticle

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