Verdoppelungsreaktionen beim Ringschluss von Peptiden. I. Synthese von Gramicidin S und von bis‐homo‐Gramicidin S aus den Pentapeptid‐Einheiten. 7. Mitteilung über homodet cyclische Polypeptide

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Abstract
Attempts to cyclize the p‐nitrophenyl esters of the pentapeptides L‐valyl‐L‐(Nδ‐tosyl)‐ornithyl‐L‐leucyl‐D‐phenylalanyl‐L‐proline and L‐valyl‐L‐(Nε‐tosyl)‐lysyl‐L‐leucyl‐D‐phenylalanyl‐L‐proline lead to a condensation and cyclization reaction of 2 molecules each of activated esters. The cyclic products are identical with those obtained from the corresponding derivatives of the linear decapeptides.This kind of doubling reaction during cyclization seems to play a greater role in the synthesis of homodetic cyclo‐polypeptides than anticipated. The phenomenon might be expected to occur especially well with peptides containing an odd number of amino acid residues.

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