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Article Abstract
We describe the first synthesis of the natural cyclic hexapeptide Fusahexin (-ala-Leu-ehr=Pro-leu-Leu) () containing the bicyclic dipeptide ehr=Pro, a tetrahydro-1,3-oxazin-4-one formed from erythronine and proline. Fusahexin and several other peptides were obtained either by using the bicyclic dipeptide Fmoc-ehr=Pro-OH () in SPPS or by late-stage oxidation of a precursor peptide aldehyde. In all cases studied, the bicyclic dipeptide ehr=Pro cyclizes by acid-promoted condensation, forming the bridge head of the fused bicyclic ring exclusively in configuration. The conformational behavior of Fusahexin and several stereochemical variants was characterized by NMR and modeling. Its convenient accessibility and its transferability make the β-turn dipeptide ehr=Pro a useful general reverse-turn dipeptide.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC12340964 | PMC |
| http://dx.doi.org/10.1021/acs.joc.5c01080 | DOI Listing |
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