Self-Assembly of Catenanes from Lasso Peptides

Lasso peptides exist naturally in a threaded state as [1]­rotaxanes, and we reasoned that lasso peptides cleaved in their loop region could serve as building blocks for catenanes. Mutagenesis of the lasso peptide microcin J25 (MccJ25) with two cysteine residues followed by cleavage of the peptide wi...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 138; no. 43; pp. 14214 - 14217
Main Authors Allen, Caitlin D, Link, A. James
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 02.11.2016
Subjects
Animals
Catenanes - chemistry
Models, Molecular
Peptides - chemistry
Protein Conformation
Temperature
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Summary:Lasso peptides exist naturally in a threaded state as [1]­rotaxanes, and we reasoned that lasso peptides cleaved in their loop region could serve as building blocks for catenanes. Mutagenesis of the lasso peptide microcin J25 (MccJ25) with two cysteine residues followed by cleavage of the peptide with trypsin led to a [2]­rotaxane structure that self-assembled into a [3]­catenane and [4]­catenanes at room temperature in aqueous solution. The [3]­catenane represents the smallest ring size of a catenane composed solely of polypeptide segments. The NMR structure of the [3]­catenane was determined, suggesting that burial of hydrophobic residues may be a driving force for assembly of the catenane structure.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b09454