Hermann, Christoph and Giammasi, Chiara and Geyer, Armin and Maier, Martin E. (2001) Syntheses of hapalosin analogs by solid-phase assembly of acyclic precursors. TETRAHEDRON, 57 (43). pp. 8999-9010. ISSN 0040-4020
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The paper details the synthesis of hapalosin analogs 4 (cyclic depsipeptides) using solid-phase chemistry. Key building blocks were the Fmoc-protected gamma -amino-beta -hydroxy acid 11 and the THP-protected syn-beta -hydroxy acids 18. The amino acid 11 was fashioned from the amine 6 which was obtained by an ADH-route. The protected amino acids 18 were prepared by Evans aldol reactions. Esterification of 18 with the Wang resin started the solid-phase assembly of the depsipeptides 25 containing all the building blocks. A final solution-phase deprotection of the amino group followed by macrolactamization completed the synthesis of the analogs 4. In one instance (compound 4aaa) the conformation was studied using ROESY NMR spectroscopy and MD simulation. This revealed an almost complete (93:7) preference for the s-cis-rotamer. (C) 2001 Elsevier Science Ltd. All rights reserved.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | RESISTANCE REVERSING ACTIVITIES; BETA-HYDROXY ACID; CONFORMATIONAL-ANALYSIS; CYCLIC DEPSIPEPTIDE; SANGLIFEHRIN-A; BIOLOGICAL-ACTIVITY; AGENT HAPALOSIN; ROTATING-FRAME; ARENASTATIN-A; AMINO-ACIDS; conformation; depsipeptides; macrocycles; NMR; peptide analogues; solid-phase synthesis |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 01 Dec 2021 15:28 |
| Last Modified: | 01 Dec 2021 15:28 |
| URI: | https://pred.uni-regensburg.de/id/eprint/41028 |
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