Marimganti, S. and Yasmeen, S. and Fischer, Daniela and Maier, Martin E. (2005) Synthesis of jasplakinolide analogues containing a novel omega-amino acid. CHEMISTRY-A EUROPEAN JOURNAL, 11 (22). pp. 6687-6700. ISSN 0947-6539, 1521-3765
Full text not available from this repository. (Request a copy)Abstract
The synthesis of the omega-amino acid 4 is described utilizing a two-dimensional synthesis strategy combined with an enzymatic differentiation of homotopic ester groups. The amino acid 4 features two non-bonded interactions that result in conformational constraints on a cyclic construct. This amino acid was incorporated into the four macrolactams 17, 22, 31, and 37. The ring in 17 and 22 is 18-membered, whereas 31 and 37 have a 19-membered ring. The pairs with the same ring size differ in a N-methyl group. For the larger macrolactams (31 and 37) conformational analysis showed that the macrocyclic rings are somewhat more rigid than in the natural lead, the depsipeptide jasplakinolide. Nevertheless, their conformations are comparable to the natural product. There are no intramolecular hydrogen bonds, neither is the cis-rotamer populated in the N-methyl compound 37. Due to the increased flexibility of the smaller macrolactams 17 and 22 and signal overlap, a distinct solution structure could not be obtained for these compounds. The amino acid 4 should be useful for restricting the conformation of other small peptides.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | N-METHYLAMINO ACIDS; GEODIAMOLIDE-A; STEREOSELECTIVE-SYNTHESIS; MARINE SPONGE; (+)-JASPLAKINOLIDE JASPAMIDE; CONFORMATIONAL-ANALYSIS; ACTIN POLYMERIZATION; PEPTIDE-SYNTHESIS; PHASE SYNTHESIS; CYCLODEPSIPEPTIDE; amino acids; conformation analysis; natural products; peptidomimetic; total synthesis |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 23 Apr 2021 07:33 |
| Last Modified: | 23 Apr 2021 07:33 |
| URI: | https://pred.uni-regensburg.de/id/eprint/35434 |
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