Lasso Peptide Benenodin‑1 Is a Thermally Actuated [1]Rotaxane Switch
Mechanically interlocked molecules that change their conformation in response to stimuli have been developed by synthetic chemists as building blocks for molecular machines. Here we describe a natural product, the lasso peptide benenodin-1, which exhibits conformational switching between two distinc...
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| Published in | Journal of the American Chemical Society Vol. 139; no. 30; pp. 10403 - 10409 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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American Chemical Society
02.08.2017
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| Abstract | Mechanically interlocked molecules that change their conformation in response to stimuli have been developed by synthetic chemists as building blocks for molecular machines. Here we describe a natural product, the lasso peptide benenodin-1, which exhibits conformational switching between two distinct threaded conformers upon actuation by heat. We have determined the structures of both conformers and have characterized the kinetics and energetics of the conformational switch. Single amino acid substitutions to benenodin-1 generate peptides that are biased to a single conformer, showing that the switching behavior is potentially an evolvable trait in these peptides. Lasso peptides such as benenodin-1 can be recognized and cleaved by enzymes called lasso peptide isopeptidases. We show that only the native conformer of benenodin-1 is cleaved by its cognate isopeptidase. Thus, thermally induced conformational switching of benenodin-1 may also be relevant to the biological function of these molecules. |
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| AbstractList | Mechanically interlocked molecules that change their conformation in response to stimuli have been developed by synthetic chemists as building blocks for molecular machines. Here we describe a natural product, the lasso peptide benenodin-1, which exhibits conformational switching between two distinct threaded conformers upon actuation by heat. We have determined the structures of both conformers and have characterized the kinetics and energetics of the conformational switch. Single amino acid substitutions to benenodin-1 generate peptides that are biased to a single conformer, showing that the switching behavior is potentially an evolvable trait in these peptides. Lasso peptides such as benenodin-1 can be recognized and cleaved by enzymes called lasso peptide isopeptidases. We show that only the native conformer of benenodin-1 is cleaved by its cognate isopeptidase. Thus, thermally induced conformational switching of benenodin-1 may also be relevant to the biological function of these molecules. Mechanically interlocked molecules that change their conformation in response to stimuli have been developed by synthetic chemists as building blocks for molecular machines. Here we describe a natural product, the lasso peptide benenodin-1, which exhibits conformational switching between two distinct threaded conformers upon actuation by heat. We have determined the structures of both conformers and have characterized the kinetics and energetics of the conformational switch. Single amino acid substitutions to benenodin-1 generate peptides that are biased to a single conformer, showing that the switching behavior is potentially an evolvable trait in these peptides. Lasso peptides such as benenodin-1 can be recognized and cleaved by enzymes called lasso peptide isopeptidases. We show that only the native conformer of benenodin-1 is cleaved by its cognate isopeptidase. Thus thermally-induced conformational switching of benenodin-1 may also be relevant to the biological function of these molecules. Authors are required to submit a graphic entry for the Table of Contents (TOC) that, in conjunction with the manuscript title, should give the reader a representative idea of one of the following: A key structure, reaction, equation, concept, or theorem, etc., that is discussed in the manuscript. Consult the journal’s Instructions for Authors for TOC graphic specifications. |
| Author | Zong, Chuhan Link, A. James Wu, Michelle J Qin, Jason Z |
| AuthorAffiliation | Department of Chemistry Department of Molecular Biology Department of Chemical and Biological Engineering |
| AuthorAffiliation_xml | – name: Department of Molecular Biology – name: Department of Chemistry – name: Department of Chemical and Biological Engineering – name: 2 Department of Molecular Biology, Princeton University, Princeton, NJ 08544 – name: 1 Department of Chemistry, Princeton University, Princeton, NJ 08544 – name: 3 Department of Chemical and Biological Engineering, Princeton University, Princeton, NJ 08544 |
| Author_xml | – sequence: 1 givenname: Chuhan surname: Zong fullname: Zong, Chuhan – sequence: 2 givenname: Michelle J orcidid: 0000-0003-1734-7994 surname: Wu fullname: Wu, Michelle J – sequence: 3 givenname: Jason Z surname: Qin fullname: Qin, Jason Z – sequence: 4 givenname: A. James orcidid: 0000-0001-5066-9691 surname: Link fullname: Link, A. James email: ajlink@princeton.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28696674$$D View this record in MEDLINE/PubMed |
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| SubjectTerms | amino acid substitution Caulobacteraceae - chemistry enzymes heat Kinetics peptides Peptides - chemistry Peptides - genetics Protein Conformation Rotaxanes - chemistry Temperature |
| Title | Lasso Peptide Benenodin‑1 Is a Thermally Actuated [1]Rotaxane Switch |
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