Tremmel, Peter and Brand, Jörg and Knapp, Volker and Geyer, Armin (2003) Side-chain-functionalized dipeptides derived from 6,5-fused bicyclic thiazolidinlactams. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (5). pp. 878-884. ISSN 1434-193X, 1099-0690
Full text not available from this repository. (Request a copy)Abstract
Condensation of D-arabinuronolactone (2) with L-cysteine methyl ester yields the bicyclic thiazolidinlactam 3 as a single diastereoisomer with the new bridgehead stereocenter in the (S) configuration. Regioselective activation of the alpha-hydroxy group leads to the triflate 4 without requiring protecting groups on the residual hydroxy groups. Subsequent azide exchange, reduction, and Boc protection, yields the epimeric dipeptide mimetics 6 and 7. Compound 3 forms the single acetonide 9, which permits the regioselective alkylation of the gamma-hydroxy group of the bicyclic framework. Subsequent deprotection and exchange of the a-hydroxy functionality against a Boc-protected amino group (13) demonstrates the regioselective side-chain modification of bicyclic dipeptides.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | AMINO-ACIDS; DESIGN; PEPTIDOMIMETICS; SCAFFOLDS; MIMETICS; PEPTIDES; peptidomimetics; heterocycles; lactams; structure elucidation; amino acids |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 24 Aug 2021 10:44 |
| Last Modified: | 24 Aug 2021 10:44 |
| URI: | https://pred.uni-regensburg.de/id/eprint/39229 |
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