Brackmann, Farina and Colombo, Noemi and Cabrele, Chiara and de Meijere, Armin (2006) An improved synthesis of 3,4-(aminomethano)proline and its incorporation into small oligopeptides. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (19). pp. 4440-4450. ISSN 1434-193X,
Full text not available from this repository. (Request a copy)Abstract
Starting from the readily available Garner aldehyde, a new synthesis of diastereomerically and enantiomerically pure 3,4-(aminomethano)prolinol (2R,l'S,3S,4S)-17 has been developed using simple and easily scalable transformations. The protected diamino alcohol (2R,l'S,3S,4S)-17 has been shown to be an appropriate compound for the exchange of protecting groups. Final Jones oxidation furnished the correspondingly protected diamino acids in high yields. The newly synthesized Fmoc/Boc-protected 3,4-(aminomethano)proline (Amp). derivatives, which are proline mimics as well as bicyclic gamma-amino acids, depending on the orthogonal protecting group pattern, were employed for solid-phase peptide synthesis with the Fmoc strategy. Thus, the features of Amp as a gamma-amino acid residue (gamma-Amp) were investigated in the preparation of alternating alpha/gamma-amino acid sequences. The obtained highly homogeneous products were characterized by circular dichroism spectroscopy. The fact that the dichroic properties of the alpha/gamma-oligopeptides were independent from the solvent used (water or methanol) suggests the presence of a preferred conformation. These results are encouraging for the development of foldamers based on gamma-Amp units.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | SHEET SECONDARY STRUCTURE; SHORT ALPHA/BETA-PEPTIDES; BETA-PEPTIDES; AMINO-ACIDS; L-PROLINE; GAMMA-PEPTIDES; HELICAL CONFORMATIONS; PHASE SYNTHESIS; FOLDAMERS; OLIGOMERS; cyclopropanes; amino acids; small ring systems; oligopeptides |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy > Pharmacology and Toxicology (Prof. Schlossmann, formerly Prof. Seifert) |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 27 Jan 2021 10:37 |
| Last Modified: | 27 Jan 2021 10:37 |
| URI: | https://pred.uni-regensburg.de/id/eprint/34012 |
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