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 (1)H 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 gamma-turn and a type II beta-turn conformation.
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http://dx.doi.org/10.1021/jo901389q | DOI Listing |
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