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

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• 作者：Karine Guitot ; Stefano Carboni ; Oliver Reiser ; Umberto Piarulli
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：November 6, 2009
• 年：2009
• 卷：74
• 期：21
• 页码：8433-8436
• 全文大小：717K
• 年卷期：v.74,no.21(November 6, 2009)
• ISSN：1520-6904

文摘

A straightforward synthesis of (S)- and (R)-N-Boc-5-oxo-piperazine-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 ¹H NMR spectroscopy. In the case of Boc-Val-(S)-PCA-Gly-Leu-OMe, two readily interconverting conformations (in a 40%:60% ratio) were observed, differing for the cis−trans isomerizaton of the tertiary amide bond, while Boc-Val-(R)-PCA-Gly-Leu-OMe displayed an equilibrium between a γ-turn and a type II β-turn conformation.