Cyclic and Lasso Peptides: Sequence Determination, Topology Analysis, and Rotaxane Formation.

TitleCyclic and Lasso Peptides: Sequence Determination, Topology Analysis, and Rotaxane Formation.
Publication TypeJournal Article
Year of Publication2018
AuthorsElashal, HE, Cohen, RD, Elashal, HE, Zong, C, A Link, J, Raj, M
JournalAngew Chem Int Ed Engl
Volume57
Issue21
Pagination6150-6154
Date Published2018 05 22
ISSN1521-3773
KeywordsChromatography, Liquid, Molecular Structure, Peptides, Rotaxanes, Tandem Mass Spectrometry
Abstract

<p>A broadly applicable chemical cleavage methodology to facilitate MS/MS sequencing was developed for macrocyclic and lasso peptides, which hold promise as exciting new therapeutics. Existing methods such as Edman degradation, CNBr cleavage, and enzymatic digestion are either limited in scope or completely fail in cleavage of constrained nonribosomal peptides. Importantly, the new method was utilized for synthesizing a unique peptide-based rotaxane (both cyclic and threaded) from the lasso peptide, benenodin-1 ΔC5.</p>

DOI10.1002/anie.201801299
Alternate JournalAngew. Chem. Int. Ed. Engl.
PubMed ID29645322
PubMed Central IDPMC6080247
Grant ListR01 GM107036 / GM / NIGMS NIH HHS / United States