c-4-Amino-t-3-hydroxy-r-1-cyclohexanecarboxylic acid and cis-4-amino-3-oxo-1-cyclohexanecarboxylic acid—mimetics of dipeptides with a twisted cis-amide bond

Add time:09/25/2019    Source:sciencedirect.com

The stereoselective synthesis of the title compounds has been performed. The relative configuration of methyl c-4-(tert-butoxycarbonylamino)-t-3-hydroxy-r-1-cyclohexanecarboxylate was confirmed by X-ray diffraction methods and its conformation in solution analyzed by NMR. The peptides containing this compound were synthesized and resolved into pure diastereoisomeric forms. Their absolute configuration was determined by independent stereospecific synthesis.

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