Global analysis of peptide cyclization efficiency.

ABSTRACT: Cyclic peptides are of considerable interest in drug discovery and nanotechnology. However, macrocyclization of peptides and other compounds has often been perceived as synthetically challenging and the cyclization yields are affected by several factors including the ring size, peptide sequence, and the reaction conditions. Through the screening of combinatorial peptide libraries, we analyzed the cyclization efficiency of >2 million peptide sequences to determine the effect of ring size, peptide sequence, and solvent on the backbone (N-to-C) cyclization of peptides. Our results show that on-resin cyclization of medium- and large-sized rings (cyclohexapeptides and above) with PyBOP is essentially quantitative for ≥ 99.96% of the sequences, with small amounts of dimer formation observed for

SUBMITTER: Thakkar A 

PROVIDER: S-EPMC3570731 | biostudies-literature | 2013 Feb

REPOSITORIES: biostudies-literature