Cyclic peptide analogs of melanocortin and amanitin and methods of making such
AssigneesThe University of British Columbia, Provincial Health Services Authority
InventorsDavid Perrin, Mihajlo Todorovic, François Bénard, Chengcheng Zhang
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Abstract
The invention described herein is based in part on the discovery of a protein/peptide crosslink, which introduces fluorescent properties, and which has been applied to synthesize analogues of melanocortin and amanitin as choice peptides to be explored in the context of isoindole peptides. Without limitation, it is expected that those trained in the art of peptide synthesis and stapling would appreciate the consequences of this invention such that other peptides of varied length can be similarly constrained by isoindole staples as featured herein.
Claims1
A compound comprising a cyclic peptide of Formula IIb wherein:
- Formula IIb has the structure:
- wherein:
- R1 is —Ac or —H;
- R2 is -Nle-;
- X1 is -His- or -D-His-;
- X2 is -Phe- or -D-Phe-;
- X3 is -Arg- or -D-Arg-;
- X4 is -Trp- or -D-Trp-;
- A1, A2, A3, A4 and A5, are each independently, hydrogen, halogen, NO2, CN, alkyne, azide, aryl, heteroaryl, COOH, SO3−, CF3, RCO, CONHR, NH2, NHR, NR2, ether, thioether, hydroxyl, or boronate;
- R is an alkyl or an alkenyl, each of which is optionally substituted;
- B1, B2, B3, B4 and B5, are each independently, carbon or nitrogen;
- and
- x and y, are each independently, a natural number between 1-15.
Dependencies are inferred from the claim text.