Stereoisomers of 4-amino-3-hydroxy-1-cyclohexanecarboxylic acid and 4-amino-3-oxo-1-cyclohexanecarboxylic acid as mimetics of a twisted cis-amide bond

Add time:07/24/2019    Source:sciencedirect.com

Stereoselective synthesis of the title compounds was performed. The relative configuration of methyl t-4-(tert-butoxycarbonylamino)-c-3-hydroxy-r-1-cyclohexanecarboxylate and methyl trans-4-(tert-butoxycarbonylamino)-3-oxo-r-1-cyclohexanecarboxylate was confirmed by X-ray diffraction methods. Analogues of cyclolinopeptide A (CLA) containing these twisted cis-amide bond mimetics were then synthesised.

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