936116-88-0Relevant articles and documents
Synthesis and structural characterization of the individual diastereoisomers of a cross-stapled alkene-bridged nisin DE-ring mimic
Slootweg, Jack C.,Kemmink, Johan,Liskamp, Rob M. J.,Rijkers, Dirk T. S.
, p. 7486 - 7496 (2013/11/06)
Herein, we describe the synthesis, structural characterization, and synthetic use as an advanced intermediate of a cross-stapled alkene-bridged hexapeptide to mimic the DE-ring of the lantibiotic nisin. The linear precursor was cyclized by ring-closing metathesis to give the correctly folded bicyclic hexapeptide in a single step, and the four individual diastereoisomers were isolated, structurally assigned and characterized by HPLC, NMR and MS, respectively. The bicyclic hexapeptide was used as a versatile advanced synthon and was modified at its C- and N-terminus, among others, with an azide moiety to access a building block suitable for Cu(i)-catalyzed alkyne-azide cycloaddition-based ligation reactions.