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Synthesis and structural study of novel dimethylcyclobutyl beta-peptides.

Article

Authorship
Elizabeth Torres ; Carles Acosta-Silva ; RÚA, FEDERICO ; Angel Alvarez-Larena ; Teodor Parella ; Vicenç Branchadell ; Rosa María Ortuño
Date
2009
Publishing House and Editing Place
PERGAMON-ELSEVIER SCIENCE LTD
Magazine
TETRAHEDRON (pp. 5669-5675) PERGAMON-ELSEVIER SCIENCE LTD
Summary Information provided by the agent in SIGEVA
The synthesis of some representative compounds of a new class of cyclobutane-containing beta-peptides starting from (-)-vernenone 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 beta3-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 th... The synthesis of some representative compounds of a new class of cyclobutane-containing beta-peptides starting from (-)-vernenone 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 beta3-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 beta-peptides adopt a hairpin-like molecular folding ruled by intermolecular hydrogen bonds in the crystal packing.
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Key Words
STUDYSTRUCTURALSYNTHESISBETA-PEPTIDEDIMETHYLCYCLOBUTYL