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- Title
Design and Synthesis of Nucleoproline Amino Acids for the Straightforward Preparation of Chiral and Conformationally Constrained Nucleopeptides.
- Authors
Kramer, Rolf A.; Bleicher, Konrad H.; Wennemers, Helma
- Abstract
A straightforward synthesis of orthogonally protected nucleoproline (Nup) amino acids and their coupling to oligomers are described. A key step is the attachment of alkynylated nucleobases to Fmoc-protected 4-azidoproline (Fmoc-Azp-OH) by a Cu-catalyzed 1,3-dipolar cycloaddition ('click reaction'). The developed protocol allows preparation of the nucleoprolines in scales of >30 g. Solid-phase peptide synthesis proved to be straightforward with these Nup amino acids. The resulting oligonucleoproline peptides adopt defined helices, are very well H2O soluble, and show comparable cell-penetrating properties as recently reported α-nucleoalanine peptides.
- Subjects
PROLINE; AMINO acids; CHIRALITY; NUCLEOPEPTIDES; OLIGOMERS
- Publication
Helvetica Chimica Acta, 2012, Vol 95, Issue 12, p2621
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201200557