Triproline analogues of Pro-Leu-Gly-NH2 with Pro/Leu and Pro/Phe chimeric amino acids in position 2

Margaret C. Evans, Rodney L. Johnson

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20 Scopus citations

Abstract

Synthesis of the cis- and trans-isomers of the proline-leucine (3-i-Pr-Pro) and proline-phenylalanine (3-Ph-Pro) chimeric amino acids was accomplished by intramolecular reductive-cycloalkylation of the appropriate azido-olefin. These chimeric amino acids were incorporated into the triprolyl analogues of Pro-Leu-Gly-NH2: Pro-cis-3-i-Pr-Pro-Pro-NH2 (3), Pro-trans-3-i-Pr-Pro-Pro-NH2 (4), Pro-cis-3-Ph-Pro-Pro-NH2 (5), Pro-trans-3-Ph-Pro-Pro-NH2 (6). (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)9801-9808
Number of pages8
JournalTetrahedron
Volume56
Issue number50
DOIs
StatePublished - Dec 8 2000

Bibliographical note

Funding Information:
This work was supported in part by an NIH grant (NS20036) to R. L. J. The authors thank Tom Crick for mass spectral analysis.

Keywords

  • Chimeric amino acids
  • Proline-leucine
  • Triproline analogue

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