An improved procedure for the synthesis of enaminones - Dimer building blocks in beta-strand mimetics
2005 (English)In: SYNTHESIS-STUTTGART, ISSN 0039-7881, Vol. 15, 2590-6 p.Article in journal (Refereed) Published
@-Tides have been shown to have the same characteristics as a peptide in the P-strand conformation and to have the ability to self-associate into dimeric beta-sheets. Aza-cyclohexaenaminones, obtained by condensation of a protected azacyclohexa-3,5-dione and amino acid esters, are the key building-blocks in the synthesis of @-tides. An improved three-step synthetic sequence to these enaminones has been developed that takes advantage of microwave-assisted chemistry in two of the steps to enhance the reaction rates. It was also found that the enaminone building blocks can be obtained by direct condensation of the aza-cyclohexa-3,5-dione with amino acid esters, without prior activation of the diketone. Multivariate design was used to optimize this microwave-assisted condensation, resulting in a short reaction time (300 s) and high yields (67-94%).
Place, publisher, year, edition, pages
2005. Vol. 15, 2590-6 p.
enaminones, beta-strand mimetics, microwave-assisted synthesis, multivariate design, optimization
IdentifiersURN: urn:nbn:se:umu:diva-13560DOI: doi:10.1055/s-2005-872094OAI: oai:DiVA.org:umu-13560DiVA: diva2:153231