Marina Schinnerl, Justin K. Murray, J. M. Langenhan
Feb 1, 2003
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0
Influential Citations
41
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Journal
European Journal of Organic Chemistry
Abstract
We report a synthesis of a protected derivative of trans-4-aminopiperidine-3-carboxylic acid (APiC). The route provides either enantiomer. All intermediates are purified by crystallization, and large-scale preparation is therefore possible. An analogous route provides either enantiomer of trans-2-aminocyclohexanecarboxylic acid (ACHC). We have previously shown that β-peptide oligomers containing ACHC adopt a helical conformation defined by 14-membered C=O(i)···H−N(i − 2) hydrogen bonds (“14-helix”). Here we show that APiC residues can be incorporated into the 14-helix. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)