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Synthesis of (S)- and (R)-5-Oxo-piperazine-2-Carboxylic Acid and Its Application to Peptidomimetics

Guitot, Karine ; Carboni, Stefano ; Reiser, Oliver ; Piarulli, Umberto



Zusammenfassung

A straightforward synthesis of (S)- and (R)-N-Boc-5-oxopiperazine-2-carboxylic acid is reported starting from L- or D-serine and ethyl glyoxylate. Those were evaluated as constituents in two tetrapeptides by studying their secondary Structure by H-1 NMR spectroscopy. In the case of Boc-Val-(S)-PCA-Gly-Leu-OMe, two readily interconverting conformations (in a 40%: 60% ratio) were observed, ...

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