Noncovalent Peptide Assembly Enables Crystalline, Permutable, and Reactive Thiol Frameworks

Hess, Selina S.; Coppola, Francesco; Dang, Viet Thuc; Tran, Phuong Nguyen; Mickel, Philip J.; Oktawiec, Julia; Ren, Zhong; Král, Petr; Nguyen, Andy I.

doi:10.1021/jacs.3c03645

Noncovalent Peptide Assembly Enables Crystalline, Permutable, and Reactive Thiol Frameworks

Journal Article · 28 August 2023 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.3c03645· OSTI ID:2423544

Hess, Selina S. ^[1]; ^[1]; Dang, Viet Thuc ^[1]; Tran, Phuong Nguyen ^[1]; Mickel, Philip J. ^[1]; ^[2]; ^[1]; ^[1]; ^[1]

Department of Chemistry, University of Illinois Chicago, Chicago, Illinois 60607, United States
Department of Chemistry, Northwestern University, Evanston, Illinois 60208, United States

Not provided.

Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: USDOE

DOE Contract Number:: AC02-06CH11357

OSTI ID:: 2423544

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 36 Vol. 145; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (68)

Thiol-based redox switches Groitl, Bastian; Jakob, Ursula Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics, Vol. 1844, Issue 8 https://doi.org/10.1016/j.bbapap.2014.03.007	journal	August 2014
Physiological functions of thioredoxin and thioredoxin reductase: Thioredoxin and thioredoxin reductase Arnér, Elias S. J.; Holmgren, Arne European Journal of Biochemistry, Vol. 267, Issue 20 https://doi.org/10.1046/j.1432-1327.2000.01701.x	journal	October 2000
An Adaptable Peptide-Based Porous Material Rabone, J.; Yue, Y. - F.; Chong, S. Y. Science, Vol. 329, Issue 5995 https://doi.org/10.1126/science.1190672	journal	August 2010
Peptide–Metal Frameworks with Metal Strings Guided by Dispersion Interactions Schnitzer, Tobias; Paenurk, Eno; Trapp, Nils Journal of the American Chemical Society, Vol. 143, Issue 2 https://doi.org/10.1021/jacs.0c11793	journal	January 2021
Targeting proteases: successes, failures and future prospects Turk, Boris Nature Reviews Drug Discovery, Vol. 5, Issue 9 https://doi.org/10.1038/nrd2092	journal	September 2006
Gradual Release of Strongly Bound Nitric Oxide from Fe ₂ (NO) ₂ (dobdc) Bloch, Eric D.; Queen, Wendy L.; Chavan, Sachin Journal of the American Chemical Society, Vol. 137, Issue 10 https://doi.org/10.1021/ja5132243	journal	March 2015
Nitric oxide release: Part I. Macromolecular scaffolds Riccio, Daniel A.; Schoenfisch, Mark H. Chemical Society Reviews, Vol. 41, Issue 10 https://doi.org/10.1039/c2cs15272j	journal	January 2012
Highly efficient and selective Hg(II) removal from water by thiol-functionalized MOF-808: Kinetic and mechanism study Ji, Chenghan; Ren, Yi; Yu, Hang Chemical Engineering Journal, Vol. 430 https://doi.org/10.1016/j.cej.2021.132960	journal	February 2022
NO-Releasing Zeolites and Their Antithrombotic Properties Wheatley, Paul S.; Butler, Anthony R.; Crane, Michael S. Journal of the American Chemical Society, Vol. 128, Issue 2 https://doi.org/10.1021/ja0503579	journal	January 2006
On the development of proton conducting polymer membranes for hydrogen and methanol fuel cells Kreuer, K. D. Journal of Membrane Science, Vol. 185, Issue 1, p. 29-39 https://doi.org/10.1016/s0376-7388(00)00632-3	journal	April 2001
Postsynthetically Modified Covalent Organic Frameworks for Efficient and Effective Mercury Removal Sun, Qi; Aguila, Briana; Perman, Jason Journal of the American Chemical Society, Vol. 139, Issue 7 https://doi.org/10.1021/jacs.6b12885	journal	February 2017
The Thiol-Michael Addition Click Reaction: A Powerful and Widely Used Tool in Materials Chemistry Nair, Devatha P.; Podgórski, Maciej; Chatani, Shunsuke Chemistry of Materials, Vol. 26, Issue 1 https://doi.org/10.1021/cm402180t	journal	September 2013
A fully automated flow-based approach for accelerated peptide synthesis Mijalis, Alexander J.; Thomas, Dale A.; Simon, Mark D. Nature Chemical Biology, Vol. 13, Issue 5 https://doi.org/10.1038/nchembio.2318	journal	February 2017
Hard and Soft Acids and Bases Pearson, Ralph G. Journal of the American Chemical Society, Vol. 85, Issue 22 https://doi.org/10.1021/ja00905a001	journal	November 1963
Calcium-induced structural changes and domain autonomy in calmodulin Finn, Bryan E.; Evenäs, Johan; Drakenberg, Torbjörn Nature Structural & Molecular Biology, Vol. 2, Issue 9 https://doi.org/10.1038/nsb0995-777	journal	September 1995
Peptide self-assembly triggered by metal ions Zou, Rongfeng; Wang, Qi; Wu, Junchen Chemical Society Reviews, Vol. 44, Issue 15 https://doi.org/10.1039/c5cs00234f	journal	January 2015
Lone Pair Functionality in Divalent Lead Compounds Shimoni-Livny, Liat; Glusker, Jenny P.; Bock, Charles W. Inorganic Chemistry, Vol. 37, Issue 8 https://doi.org/10.1021/ic970909r	journal	April 1998
Argentophilic Interactions Schmidbaur, Hubert; Schier, Annette Angewandte Chemie International Edition, Vol. 54, Issue 3 https://doi.org/10.1002/anie.201405936	journal	November 2014
Artificial Metal–Peptide Assemblies: Bioinspired Assembly of Peptides and Metals through Space and across Length Scales Dong, Jinqiao; Liu, Yan; Cui, Yong Journal of the American Chemical Society, Vol. 143, Issue 42 https://doi.org/10.1021/jacs.1c08487	journal	October 2021
High-Capacity Hydrogen and Nitric Oxide Adsorption and Storage in a Metal−Organic Framework Xiao, Bo; Wheatley, Paul S.; Zhao, Xuebo Journal of the American Chemical Society, Vol. 129, Issue 5 https://doi.org/10.1021/ja066098k	journal	February 2007
X‐ray Crystallographic Observation of Chiral Transformations within a Metal–Peptide Pore Saito, Ami; Sawada, Tomohisa; Fujita, Makoto Angewandte Chemie International Edition, Vol. 59, Issue 46 https://doi.org/10.1002/anie.202007731	journal	September 2020
Structural Basis for the Selective Pb(II) Recognition of Metalloregulatory Protein PbrR691 Huang, Shanqing; Liu, Xichun; Wang, Dan Inorganic Chemistry, Vol. 55, Issue 24 https://doi.org/10.1021/acs.inorgchem.6b02397	journal	November 2016
Metal‐Helix Frameworks from Short Hybrid Peptide Foldamers Misra, Rajkumar; Saseendran, Abhijith; Dey, Sanjit Angewandte Chemie International Edition, Vol. 58, Issue 8 https://doi.org/10.1002/anie.201810849	journal	February 2019
Chiral II−VI Semiconductor Nanostructure Superlattices Based on an Amino Acid Ligand Rebilly, Jean-Noël; Gardner, Paul W.; Darling, George R. Inorganic Chemistry, Vol. 47, Issue 20 https://doi.org/10.1021/ic801097w	journal	September 2008
Assembly of π-Stacking Helical Peptides into a Porous and Multivariable Proteomimetic Framework Heinz-Kunert, Sherrie L.; Pandya, Ashma; Dang, Viet Thuc Journal of the American Chemical Society, Vol. 144, Issue 15 https://doi.org/10.1021/jacs.2c02146	journal	April 2022
Side-chain control of porosity closure in single- and multiple-peptide-based porous materials by cooperative folding Martí-Gastaldo, C.; Antypov, D.; Warren, J. E. Nature Chemistry, Vol. 6, Issue 4 https://doi.org/10.1038/nchem.1871	journal	February 2014
Highly selective removal of Hg 2+ and Pb 2+ by thiol-functionalized Fe 3 O 4 @metal-organic framework core-shell magnetic microspheres Ke, Fei; Jiang, Jing; Li, Yizhi Applied Surface Science, Vol. 413 https://doi.org/10.1016/j.apsusc.2017.03.303	journal	August 2017
Nitric oxide release: Part II. Therapeutic applications Carpenter, Alexis W.; Schoenfisch, Mark H. Chemical Society Reviews, Vol. 41, Issue 10 https://doi.org/10.1039/c2cs15273h	journal	January 2012
Aqueous-sensitive reaction sites in sulfonic acid-functionalized mesoporous silicas Morales, G.; Athens, G.; Chmelka, B. Journal of Catalysis, Vol. 254, Issue 2 https://doi.org/10.1016/j.jcat.2007.12.011	journal	March 2008
Thiol-ene “click” reactions and recent applications in polymer and materials synthesis Lowe, Andrew B. Polym. Chem., Vol. 1, Issue 1 https://doi.org/10.1039/b9py00216b	journal	January 2010
Dense thiol arrays for metal–organic frameworks: boiling water stability, Hg removal beyond 2 ppb and facile crosslinking Li, Mu-Qing; Wong, Yan-Lung; Lum, Tsz-Shan Journal of Materials Chemistry A, Vol. 6, Issue 30 https://doi.org/10.1039/c8ta04020f	journal	January 2018
Structure and Chemistry of Cytochrome P450 Denisov, Ilia G.; Makris, Thomas M.; Sligar, Stephen G. ChemInform, Vol. 36, Issue 37 https://doi.org/10.1002/chin.200537282	journal	September 2005
Enhanced rare-earth separation with a metal-sensitive lanmodulin dimer Mattocks, Joseph A.; Jung, Jonathan J.; Lin, Chi-Yun Nature, Vol. 618, Issue 7963 https://doi.org/10.1038/s41586-023-05945-5	journal	May 2023
Guest Molecule-Mediated Energy Harvesting in a Conformationally Sensitive Peptide–Metal Organic Framework Chen, Yu; Guerin, Sarah; Yuan, Hui Journal of the American Chemical Society, Vol. 144, Issue 8 https://doi.org/10.1021/jacs.1c11750	journal	January 2022
A robust MOF-based trap with high-density active alkyl thiol for the super-efficient capture of mercury Yang, Pengfei; Shu, Yufang; Zhuang, Qixin Chemical Communications, Vol. 55, Issue 86 https://doi.org/10.1039/c9cc06255f	journal	January 2019
Effective Mercury Sorption by Thiol-Laced Metal–Organic Frameworks: in Strong Acid and the Vapor Phase Yee, Ka-Kit; Reimer, Nele; Liu, Jie Journal of the American Chemical Society, Vol. 135, Issue 21 https://doi.org/10.1021/ja400212k	journal	May 2013
Ribonucleotide Reductases Nordlund, Pär; Reichard, Peter Annual Review of Biochemistry, Vol. 75, Issue 1 https://doi.org/10.1146/annurev.biochem.75.103004.142443	journal	June 2006
Thiol-Based Redox Switches and Gene Regulation Antelmann, Haike; Helmann, John D. Antioxidants & Redox Signaling, Vol. 14, Issue 6 https://doi.org/10.1089/ars.2010.3400	journal	March 2011
Coiled-coils: The long and short of it Truebestein, Linda; Leonard, Thomas A. BioEssays, Vol. 38, Issue 9 https://doi.org/10.1002/bies.201600062	journal	August 2016
Polystyrene sulphonic acid resins with enhanced acid strength via macromolecular self-assembly within confined nanospace Zhang, Xiaomin; Zhao, Yaopeng; Xu, Shutao Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms4170	journal	January 2014
Biomimetic peptide self-assembly for functional materials Levin, Aviad; Hakala, Tuuli A.; Schnaider, Lee Nature Reviews Chemistry, Vol. 4, Issue 11 https://doi.org/10.1038/s41570-020-0215-y	journal	September 2020
Peptide Metal–Organic Frameworks for Enantioselective Separation of Chiral Drugs Navarro-Sánchez, José; Argente-García, Ana I.; Moliner-Martínez, Yolanda Journal of the American Chemical Society, Vol. 139, Issue 12 https://doi.org/10.1021/jacs.7b00280	journal	March 2017
Mercury nano-trap for effective and efficient removal of mercury(II) from aqueous solution Li, Baiyan; Zhang, Yiming; Ma, Dingxuan Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms6537	journal	November 2014
Reactions of electrophiles with nucleophilic thiolate sites: relevance to pathophysiological mechanisms and remediation LoPachin, Richard M.; Gavin, Terrence Free Radical Research, Vol. 50, Issue 2 https://doi.org/10.3109/10715762.2015.1094184	journal	November 2015
Redox Signaling by Reactive Electrophiles and Oxidants Parvez, Saba; Long, Marcus J. C.; Poganik, Jesse R. Chemical Reviews, Vol. 118, Issue 18 https://doi.org/10.1021/acs.chemrev.7b00698	journal	August 2018
Thiol-functionalized Zr metal-organic frameworks for efficient removal of Fe3+ from water Yuan, Yufei; Yu, Junting; Chen, Huanhuan Cell Reports Physical Science, Vol. 3, Issue 3 https://doi.org/10.1016/j.xcrp.2022.100783	journal	March 2022
Supramolecular Assembly of Peptide Amphiphiles Hendricks, Mark P.; Sato, Kohei; Palmer, Liam C. Accounts of Chemical Research, Vol. 50, Issue 10 https://doi.org/10.1021/acs.accounts.7b00297	journal	September 2017
Cysteine-Mediated Redox Signaling: Chemistry, Biology, and Tools for Discovery Paulsen, Candice E.; Carroll, Kate S. Chemical Reviews, Vol. 113, Issue 7 https://doi.org/10.1021/cr300163e	journal	March 2013
383. The oxidation–reduction potentials of some copper complexes James, B. R.; Williams, R. J. P. J. Chem. Soc., Vol. 0, Issue 0 https://doi.org/10.1039/jr9610002007	journal	January 1961
Thiol functionalized covalent organic framework for highly selective enrichment and detection of mercury by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry Sun, Qianqian; Ma, Wende; Dan, Ouyang The Analyst, Vol. 146, Issue 9 https://doi.org/10.1039/d1an00282a	journal	January 2021
Electronic Structures of Metal Sites in Proteins and Models: Contributions to Function in Blue Copper Proteins Solomon, Edward I.; Szilagyi, Robert K.; DeBeer George, Serena Chemical Reviews, Vol. 104, Issue 2 https://doi.org/10.1021/cr0206317	journal	February 2004
Thiol-functionalized metal–organic frameworks embedded with chelator-modified magnetite for high-efficiency and recyclable mercury removal in aqueous solutions Li, Yuliang; Tan, Mengxi; Liu, Guangxia Journal of Materials Chemistry A, Vol. 10, Issue 12 https://doi.org/10.1039/d1ta10906e	journal	January 2022
Iron/sulfur proteins biogenesis in prokaryotes: Formation, regulation and diversity Roche, Béatrice; Aussel, Laurent; Ezraty, Benjamin Biochimica et Biophysica Acta (BBA) - Bioenergetics, Vol. 1827, Issue 3 https://doi.org/10.1016/j.bbabio.2012.12.010	journal	March 2013
Aromatic Polymer with Pendant Perfluoroalkyl Sulfonic Acid for Fuel Cell Applications Yoshimura, Ken; Iwasaki, Katsuhiko Macromolecules, Vol. 42, Issue 23 https://doi.org/10.1021/ma901953e	journal	October 2009
Chemical control of structure and guest uptake by a conformationally mobile porous material Katsoulidis, Alexandros P.; Antypov, Dmytro; Whitehead, George F. S. Nature, Vol. 565, Issue 7738 https://doi.org/10.1038/s41586-018-0820-9	journal	January 2019
De Novo Design of Helical Bundles as Models for Understanding Protein Folding and Function Hill, R. Blake; Raleigh, Daniel P.; Lombardi, Angela Accounts of Chemical Research, Vol. 33, Issue 11 https://doi.org/10.1021/ar970004h	journal	November 2000
Cytochrome P450 enzymes in drug metabolism: Regulation of gene expression, enzyme activities, and impact of genetic variation Zanger, Ulrich M.; Schwab, Matthias Pharmacology & Therapeutics, Vol. 138, Issue 1 https://doi.org/10.1016/j.pharmthera.2012.12.007	journal	April 2013
Metallothionein Hamer, Dean H. Annual Review of Biochemistry, Vol. 55, Issue 1 https://doi.org/10.1146/annurev.bi.55.070186.004405	journal	June 1986
High-Efficiency Solid Phase Peptide Synthesis ( HE -SPPS) Collins, Jonathan M.; Porter, Keith A.; Singh, Sandeep K. Organic Letters, Vol. 16, Issue 3 https://doi.org/10.1021/ol4036825	journal	January 2014
Thiol-Functionalized Pores via Post-Synthesis Modification in a Metal–Organic Framework with Selective Removal of Hg(II) in Water Li, Gao-Peng; Zhang, Kun; Zhang, Peng-Feng Inorganic Chemistry, Vol. 58, Issue 5 https://doi.org/10.1021/acs.inorgchem.8b03505	journal	February 2019
New Insights into Perfluorinated Sulfonic-Acid Ionomers Kusoglu, Ahmet; Weber, Adam Z. Chemical Reviews, Vol. 117, Issue 3 https://doi.org/10.1021/acs.chemrev.6b00159	journal	January 2017
Novel sulfhydryl functionalized covalent organic frameworks for ultra-trace Hg2+ removal from aqueous solution Pan, Fei; Tong, Chunyi; Wang, Zhaoyang Journal of Materials Science & Technology, Vol. 93 https://doi.org/10.1016/j.jmst.2021.04.013	journal	December 2021
Self-Assembling Cages from Coiled-Coil Peptide Modules Fletcher, J. M.; Harniman, R. L.; Barnes, F. R. H. Science, Vol. 340, Issue 6132 https://doi.org/10.1126/science.1233936	journal	April 2013
A Perfluoroaryl-Cysteine S _N Ar Chemistry Approach to Unprotected Peptide Stapling Spokoyny, Alexander M.; Zou, Yekui; Ling, Jingjing J. Journal of the American Chemical Society, Vol. 135, Issue 16 https://doi.org/10.1021/ja400119t	journal	April 2013
Sulfur in Dynamic Covalent Chemistry Orrillo, A. Gastón; Furlan, Ricardo L. E. Angewandte Chemie International Edition, Vol. 61, Issue 26 https://doi.org/10.1002/anie.202201168	journal	May 2022
A tale of two gases: NO and H2S, foes or friends for life? Kolluru, Gopi K.; Shen, Xinggui; Kevil, Christopher G. Redox Biology, Vol. 1, Issue 1 https://doi.org/10.1016/j.redox.2013.05.001	journal	January 2013
Thiol-Based Redox Switches in Eukaryotic Proteins Brandes, Nicolas; Schmitt, Sebastian; Jakob, Ursula Antioxidants & Redox Signaling, Vol. 11, Issue 5 https://doi.org/10.1089/ars.2008.2285	journal	May 2009
A triaxial supramolecular weave Lewandowska, Urszula; Zajaczkowski, Wojciech; Corra, Stefano Nature Chemistry, Vol. 9, Issue 11 https://doi.org/10.1038/nchem.2823	journal	July 2017

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