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The study reveals the synthesis of fusahexin and characterizes its conformational behavior and cyclization in peptides.
We describe the first synthesis of the natural cyclic hexapeptide Fusahexin cyclo(-ala-Leu-ehr=Pro-leu-Leu) (1) 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 (2) 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 R 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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Bäuerlein et al. (2025) studied this question.
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