Ressurreicao, Ana Sofia M. and Bordessa, Andrea and Civera, Monica and Belvisi, Laura and Gennari, Cesare and Piarulli, Umberto (2008) Synthesis and conformational studies of peptidomimetics containing a new bifunctional diketopiperazine scaffold acting as a beta-hairpin inducer. JOURNAL OF ORGANIC CHEMISTRY, 73 (2). pp. 652-660. ISSN 0022-3263,
Full text not available from this repository. (Request a copy)Abstract
A practical synthesis of a new bifunctional diketopiperazine (DKP) scaffold 1, formally derived from the cyclization of L-aspartic acid and (S)-2,3-diaminopropionic acid, is reported. DKP-1 bears a carboxylic acid and an amino functionalities in a cis relationship, which have been used to grow peptide sequences. Tetra-, penta-, and hexapeptidomimetic sequences were prepared by solution-phase peptide synthesis (Boc strategy). Conformational analysis of these derivatives was carried out by a combination of H-1 NMR spectroscopy, IR spectroscopy, CD spectroscopy, and computer modeling, and reveals the formation of P-hairpin mimics involving 10-membered and 18-membered H-bonded rings and a reverse turn of the growing peptide chain.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PROTEINOGENIC SIDE-CHAINS; SOLUTION-PHASE SYNTHESIS; AMINO-ACIDS; COMBINATORIAL CHEMISTRY; SECONDARY STRUCTURES; DIPEPTIDE MIMICS; BICYCLIC LACTAMS; HYDROGEN-BOND; PEPTIDES; DESIGN; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 11 Nov 2020 06:10 |
| Last Modified: | 11 Nov 2020 06:10 |
| URI: | https://pred.uni-regensburg.de/id/eprint/31502 |
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