Cyclols, cyclodepsipeptides, and N-acyl-diketopiperazines from linear precursors: Synthesis and crystal structure of 10-membered cyclodepsipeptides
- 12 January 2009
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 22 (4) , 410-421
- https://doi.org/10.1111/j.1399-3011.1983.tb02110.x
Abstract
In order to investigate the relative formation tendency of different tautomeric ring systems (cyclols, cyclodepsipeptides and corresponding N-acyl-diketopiperazines), 2 linear peptide precursors containing proline as C-terminal residue, were synthesized and subjected to cyclizing conditions. Boc-Ser-Phe-Pro-ONp gave 3 isomeric cyclic compounds: .**GRAPHIC**. N-(Boc-Ser)-cyclo-(Phe-D-Pro) and the corresponding aza-cyclo. Starting from Hyb-Phe-Pro-ONp [Hyb = RS-3-hydroxybutyric acid] 2 epimeric N(3-hydroxybutyryl) diketopiperazines and the corresponding 10-membered cyclodepsipeptide (VIII) could be isolated. Crystal and molecular structure of VIII is reported.Keywords
This publication has 15 references indexed in Scilit:
- Synthesis and x-ray crystal structure of a tripeptidic cyclolTetrahedron Letters, 1981
- Cyclization of activated N-benzyloxycarbonyl-tripeptidesTetrahedron Letters, 1978
- Structure and conformation of cyclo(tri-L-prolyl) in the crystalline stateJournal of the American Chemical Society, 1976
- Eine neue Cyclolestersynthese zum Aufbau von Ergot-Peptidalkaloiden 82. Mitt. über MutterkornalkaloideMonatshefte für Chemie / Chemical Monthly, 1976
- The crystal structure and molecular conformation of cyclo-L-prolyl-L-prolyl-L-hydroxyproline, a cyclic tripeptideActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1975
- Evidence for a base catalyzed interconversion of azacyclols derived from N-(acylalanyl)-phenylalanyl-prolin-lactamsCellular and Molecular Life Sciences, 1975
- CYCLOLS-FORMATION FROM TRIPEPTIDE SYSTEMS AND STRUCTURE ASSIGNMENT BY CARBON-13 NUCLEAR MAGNETIC RESONANCEInternational Journal of Peptide and Protein Research, 1973
- Ein neues Alkaloid aus dem Mycel einesClaviceps purpurea-Stammes. Zur Biogenese von ErgocristinCellular and Molecular Life Sciences, 1973
- Synthesis of cyclols from some small peptides via amide–amide reactionJournal of the Chemical Society D: Chemical Communications, 1971
- The formation of cyclols from N-hydroxyacyllactamsTetrahedron, 1963