Stereoselective Synthesis of Molecular Square and Granny Knots.

ABSTRACT: We report on the stereoselective synthesis of both molecular granny and square knots through the use of lanthanide-complexed overhand knots of specific handedness as three-crossing "entanglement synthons". The composite knots are assembled by combining two entanglement synthons (of the same chirality for a granny knot; of opposite handedness for a square knot) in three synthetic steps: first, a CuAAC reaction joins together one end of each overhand knot. Ring-closing olefin metathesis (RCM) then affords the closed-loop knot, locking the topology. This allows the lanthanide ions necessary for stabilizing the entangled conformation of the synthons to subsequently be removed. The composite knots were characterized by ¹H and ¹³C NMR spectroscopy and mass spectrometry and

SUBMITTER: Leigh DA 

PROVIDER: S-EPMC6492950 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature