Synthesis and structural study of novel dimethylcyclobutyl β-peptides

Elisabeth Torres, Carles Acosta-Silva, Federico Rúa, Ángel Álvarez-Larena, Teodor Parella, Vicenç Branchadell, Rosa M. Ortuño

Research output: Contribution to journalArticleResearchpeer-review

26 Citations (Scopus)

Abstract

The synthesis of some representative compounds of a new class of cyclobutane-containing β-peptides starting from (-)-verbenone as a chiral precursor is presented. In these products, the cyclobutane moiety is not a part of the peptide backbone but a bulky substituent at the β3-position. These compounds have been carefully characterized and studied on the basis of the combined use of several experimental techniques together with molecular modeling by means of theoretical calculations. In the solid state, the non-cyclic β-peptides adopt a hairpin-like molecular folding ruled by intermolecular hydrogen bonds in the crystal packing. © 2009 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)5669-5675
JournalTetrahedron
Volume65
Issue number29-30
DOIs
Publication statusPublished - 18 Jul 2009

Keywords

  • β-Peptides
  • Crystal structure
  • Cyclobutanes
  • Hydrogen bonds

Fingerprint Dive into the research topics of 'Synthesis and structural study of novel dimethylcyclobutyl β-peptides'. Together they form a unique fingerprint.

Cite this