Synthesis, biological activity and molecular modelling of the 53-54 ketomethylene analogue of HEL(52-61)
Résumé
The synthesis of the 53-54 ketomethylene isostere of HEL(52-61), an antigenic decapeptide, was realised by convergent Fmoc solid-phase peptide synthesis. In addition to the target peptide, an unexpected hydroxysuccinyl by-product was recovered. The two ketomethylene epimers did not exhibit any stimulating or competitive activity. Molecular modelling studies of the analogues-MHC-II I-Ak complex suggested a departure from the canonical polyproline II conformation which could account for the absence of binding to I- Ak molecule
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