Cyclic arylopeptoid oligomers: synthesis and conformational propensities of peptide-mimetic aromatic macrocycles

Masahide Hayakawa, Ayaka Ohsawa, Kumi Takeda, Ryo Torii, Yoshiaki Kitamura, Hiroshi Katagiri and Masato Ikeda

Org. Biomol. Chem., 2018, 16, 8505
DOI: 10.1039/C8OB01962B

Bead-based screening in chemical biology and drug discovery

Vitaly V. Komnatnyy, Thomas E. Nielsen and Katrine Qvortrup

Chem. Commun., 2018, 54, 6759
DOI: 10.1039/C8CC02486C

Twisted amide electrophiles enable cyclic peptide sequencing

Serge Zaretsky, Vishal Rai, Gerald Gish, Matthew W. Forbes, Michael Kofler, Joy C. Y. Yu, Joanne Tan, Jennifer L. Hickey, Tony Pawson and Andrei K. Yudin

Org. Biomol. Chem., 2015, 13, 7384
DOI: 10.1039/C5OB01050K

Ring size effect on the solid state assembly of propargyl substituted hexa- and octacyclic peptoids

Consiglia Tedesco, Alessandra Meli, Eleonora Macedi, Veronica Iuliano, Antonio G. Ricciardulli, Francesco De Riccardis, Gavin B. M. Vaughan, Vincent J. Smith, Leonard J. Barbour and Irene Izzo

CrystEngComm, 2016, 18, 8838
DOI: 10.1039/C6CE01800A

Asymmetric synthesis of vinylogous β-amino acids and their incorporation into mixed backbone oligomers

Hao Wu, Hongchan An, Shuting (Cynthia) Mo and Thomas Kodadek

Org. Biomol. Chem., 2017, 15, 3255
DOI: 10.1039/C7OB00333A

Bio-instructive materials on-demand – combinatorial chemistry of peptoids, foldamers, and beyond

Claudine Nicole Herlan, Dominik Feser, Ute Schepers and Stefan Bräse

Chem. Commun., 2021, 57, 11131
DOI: 10.1039/D1CC04237H

Oxidation-guided and collision-induced linearization assists de novo sequencing of thioether macrocyclic peptides

Ayaka Hayashi, Yuki Goto, Yutaro Saito, Hiroaki Suga, Jumpei Morimoto and Shinsuke Sando

Chem. Commun., 2024, 60, 9436
DOI: 10.1039/D4CC03179B

Design and Facile Solid-Phase Synthesis of Conformationally Constrained Bicyclic Peptoids

Ji Hoon Lee, Han-Sung Kim and Hyun-Suk Lim

Org. Lett., 2011, 13, 5012
DOI: 10.1021/ol201773f

Heteroaryl Rings in Peptide Macrocycles

Ivan V. Smolyar, Andrei K. Yudin and Valentine G. Nenajdenko

Chem. Rev., 2019, 119, 10032
DOI: 10.1021/acs.chemrev.8b00789

Graphical and SERS dual-modal identifier for encoding OBOC library

Homan Kang, Yul Koh, Sinyoung Jeong, Chulhwan Jeong, Myeong Geun Cha, Min-Hye Oh, Jin-Kyoung Yang, Hyunmi Lee, Dae Hong Jeong, Bong-Hyun Jun, Hyejin Chang, Yong-Kweon Kim and Yoon-Sik Lee

Sensors and Actuators B: Chemical, 2020, 303, 127211
DOI: 10.1016/j.snb.2019.127211

Peptoid Polymers: A Highly Designable Bioinspired Material

Jing Sun and Ronald N. Zuckermann

ACS Nano, 2013, 7, 4715
DOI: 10.1021/nn4015714

Evaluation of the cell permeability of bicyclic peptoids and bicyclic peptide-peptoid hybrids

Hee Myeong Wang, Chang Deok Seo, Kang Ju Lee, Jun Hyung Park and Hyun-Suk Lim

Bioorganic Chemistry, 2022, 127, 105976
DOI: 10.1016/j.bioorg.2022.105976

Developments with bead-based screening for novel drug discovery

Dehua Pei and George Appiah Kubi

Expert Opinion on Drug Discovery, 2019, 14, 1097
DOI: 10.1080/17460441.2019.1647164

A solid-phase method for synthesis of dimeric and trimeric ligands: Identification of potent bivalent ligands of 14-3-3σ

Yeongju Lee, Brian Chung, Daseul Ko and Hyun-Suk Lim

Bioorganic Chemistry, 2019, 91, 103141
DOI: 10.1016/j.bioorg.2019.103141

Cyclization of peptoids by formation of boronate esters

Sara Chirayil and Kevin J. Luebke

Tetrahedron Letters, 2012, 53, 726
DOI: 10.1016/j.tetlet.2011.12.002

One-Bead–Two-Compound Thioether Bridged Macrocyclic γ-AApeptide Screening Library against EphA2

Yan Shi, Sridevi Challa, Peng Sang, Fengyu She, Chunpu Li, Geoffrey M. Gray, Alekhya Nimmagadda, Peng Teng, Timothy Odom, Yan Wang, Arjan van der Vaart, Qi Li and Jianfeng Cai

J. Med. Chem., 2017, 60, 9290
DOI: 10.1021/acs.jmedchem.7b01280

Design and synthesis of a DNA-encoded combinatorial library of bicyclic peptoids

Kang Ju Lee, Geul Bang, Yong Wook Kim, Min Hyeon Shin and Hyun-Suk Lim

Bioorganic & Medicinal Chemistry, 2021, 48, 116423
DOI: 10.1016/j.bmc.2021.116423

Peptoids with Substituents on the Backbone Carbons as Conformationally Constrained Synthetic Oligoamides

Jumpei Morimoto and Shinsuke Sando

J. Synth. Org. Chem. Jpn., 2020, 78, 1076
DOI: 10.5059/yukigoseikyokaishi.78.1076

Molecular Engineering of the Peptoid Nanosheet Hydrophobic Core

Ellen J. Robertson, Caroline Proulx, Jessica K. Su, Rita L. Garcia, Stan Yoo, Eric M. Nehls, Michael D. Connolly, Laudann Taravati and Ronald N. Zuckermann

Langmuir, 2016, 32, 11946
DOI: 10.1021/acs.langmuir.6b02735

Structure–Rheology Relationship in Nanosheet-Forming Peptoid Monolayers

Ellen J. Robertson, Eric Michael Nehls and Ronald N. Zuckermann

Langmuir, 2016, 32, 12146
DOI: 10.1021/acs.langmuir.6b02736

A Sequential Ugi Multicomponent/Cu-Catalyzed Azide–Alkyne Cycloaddition Approach for the Continuous Flow Generation of Cyclic Peptoids

Carlos Eduardo M. Salvador, Bartholomäus Pieber, Philipp M. Neu, Ana Torvisco, Carlos Kleber Z. Andrade and C. Oliver Kappe

J. Org. Chem., 2015, 80, 4590
DOI: 10.1021/acs.joc.5b00445

De Novo Sequencing of Synthetic Bis-cysteine Peptide Macrocycles Enabled by “Chemical Linearization” of Compound Mixtures

Zhi’ang Chen, Yi Wee Lim, Jin Yong Neo, Rachel Shu Ting Chan, Li Quan Koh, Tsz Ying Yuen, Yee Hwee Lim, Charles W. Johannes and Zachary P. Gates

Anal. Chem., 2023, 95, 14870
DOI: 10.1021/acs.analchem.3c01742

Development of Spiroligomer–Peptoid Hybrids

Justin D. Northrup, Giulia Mancini, Claire R. Purcell and Christian E. Schafmeister

J. Org. Chem., 2017, 82, 13020
DOI: 10.1021/acs.joc.7b01956

Incorporation of Heterocycles into the Backbone of Peptoids to Generate Diverse Peptoid-Inspired One Bead One Compound Libraries

Animesh Aditya and Thomas Kodadek

ACS Comb. Sci., 2012, 14, 164
DOI: 10.1021/co200195t

Supramolecular Nanosheets Assembled from Poly(ethylene glycol)-b-poly(N-(2-phenylethyl)glycine) Diblock Copolymer Containing Crystallizable Hydrophobic Polypeptoid: Crystallization Driven Assembly Transition from Filaments to Nanosheets

Yuhan Wei, Jiliang Tian, Zekun Zhang, Chenhui Zhu, Jing Sun and Zhibo Li

Macromolecules, 2019, 52, 1546
DOI: 10.1021/acs.macromol.8b02230

Recent Advances in the Synthesis of Peptoid Macrocycles

Alexandra M. Webster and Steven L. Cobb

Chemistry A European J, 2018, 24, 7560
DOI: 10.1002/chem.201705340

Facile Method To Sequence Cyclic Peptides/Peptoids via One-Pot Ring-Opening/Cleavage Reaction

Kang Ju Lee and Hyun-Suk Lim

Org. Lett., 2014, 16, 5710
DOI: 10.1021/ol502788e

A Chemical Inhibitor of the Skp2/p300 Interaction that Promotes p53‐Mediated Apoptosis

Misook Oh, Ji Hoon Lee, Heejo Moon, Yu‐Jung Hyun and Hyun‐Suk Lim

Angewandte Chemie, 2016, 128, 612
DOI: 10.1002/ange.201508716

Macrocyclization enhances affinity of chemokine‐binding peptoids

Kevin Brahm, Julia S. Wack, Stefanie Eckes, Victoria Engemann and Katja Schmitz

Biopolymers, 2019, 110
DOI: 10.1002/bip.23244

A Convenient Approach to Prepare Topologically Segregated Bilayer Beads for One-Bead Two-Compound Combinatorial Peptide Libraries

François Bédard, Anick Girard and Éric Biron

Int J Pept Res Ther, 2013, 19, 13
DOI: 10.1007/s10989-012-9316-x

Practical Ring-Opening Strategy for the Sequence Determination of Cyclic Peptides from One-Bead-One-Compound Libraries

Xinxia Liang, Anick Girard and Eric Biron

ACS Comb. Sci., 2013, 15, 535
DOI: 10.1021/co4000979

A Chemical Inhibitor of the Skp2/p300 Interaction that Promotes p53‐Mediated Apoptosis

Misook Oh, Ji Hoon Lee, Heejo Moon, Yu‐Jung Hyun and Hyun‐Suk Lim

Angew Chem Int Ed, 2016, 55, 602
DOI: 10.1002/anie.201508716

Oxazolidinone-Mediated Sequence Determination of One-Bead One-Compound Cyclic Peptide Libraries

Hader E. Elashal, Ryan D. Cohen, Heidi E. Elashal and Monika Raj

Org. Lett., 2018, 20, 2374
DOI: 10.1021/acs.orglett.8b00717

Comparison of Cell Permeability of Cyclic Peptoids and Linear Peptoids

Min-Kyung Shin, Yu-Jung Hyun, Ji Hoon Lee and Hyun-Suk Lim

ACS Comb. Sci., 2018, 20, 237
DOI: 10.1021/acscombsci.7b00194

Ultra-large chemical libraries for the discovery of high-affinity peptide binders

Anthony J. Quartararo, Zachary P. Gates, Bente A. Somsen, Nina Hartrampf, Xiyun Ye, Arisa Shimada, Yasuhiro Kajihara, Christian Ottmann and Bradley L. Pentelute

Nat Commun, 2020, 11
DOI: 10.1038/s41467-020-16920-3

One-Pot Photochemical Ring-Opening/Cleavage Approach for the Synthesis and Decoding of Cyclic Peptide Libraries

Xinxia Liang, Simon Vézina-Dawod, François Bédard, Karine Porte and Eric Biron

Org. Lett., 2016, 18, 1174
DOI: 10.1021/acs.orglett.6b00296

Facile Solid-Phase Parallel Synthesis of Linear and Cyclic Peptoids for Comparative Studies of Biological Activity

Shinae Park and Yong-Uk Kwon

ACS Comb. Sci., 2015, 17, 196
DOI: 10.1021/co5001647

A cleavable scaffold strategy for the synthesis of one-bead one-compound cyclic peptoid libraries that can be sequenced by tandem mass spectrometry

Levi S. Simpson and Thomas Kodadek

Tetrahedron Letters, 2012, 53, 2341
DOI: 10.1016/j.tetlet.2012.02.112

Design and Synthesis of a Novel N-(1H-tetrazol-5-yl)methyl Cyclic Peptoid Using Nosyl-protected N-(1-trityl-1H-tetrazol-5-yl)methyl Substituted Glycine

Girish Prabhu, M. Krishnamurthy, M. Samarasimhareddy, N. Narendra and Vommina V. Sureshbabu

Int J Pept Res Ther, 2017, 23, 493
DOI: 10.1007/s10989-017-9581-9

Synthesis and Screening of Stereochemically Diverse Combinatorial Libraries of Peptide Tertiary Amides

Yu Gao and Thomas Kodadek

Chemistry & Biology, 2013, 20, 360
DOI: 10.1016/j.chembiol.2013.01.013

Potential pharmacological chaperones targeting cancer-associated MCL-1 and Parkinson disease-associated α-synuclein

Misook Oh, Ji Hoon Lee, Wei Wang, Hui Sun Lee, Woo Sirl Lee, Christopher Burlak, Wonpil Im, Quyen Q. Hoang and Hyun-Suk Lim

Proc. Natl. Acad. Sci. U.S.A., 2014, 111, 11007
DOI: 10.1073/pnas.1320556111

Affinity selection–mass spectrometry with linearizable macrocyclic peptide libraries

Michael A. Lee, Joseph S. Brown, Charlotte E. Farquhar, Andrei Loas and Bradley L. Pentelute

Sci. Adv., 2025, 11
DOI: 10.1126/sciadv.adr1018

Combinatorial Chemistry Online

N.K. Terrett

Combinatorial Chemistry - an Online Journal, 2011, 13, 9
DOI: 10.1016/j.comche.2011.02.001

CycLS: Accurate, whole-library sequencing of cyclic peptides using tandem mass spectrometry

Chad Townsend, Akihiro Furukawa, Joshua Schwochert, Cameron R. Pye, Quinn Edmondson and R. Scott Lokey

Bioorganic & Medicinal Chemistry, 2018, 26, 1232
DOI: 10.1016/j.bmc.2018.01.027

Oligomers of α‐ABpeptoid/β3‐peptide hybrid

Kang Ju Lee, Ganesh A. Sable, Min‐Kyung Shin and Hyun‐Suk Lim

Biopolymers, 2019, 110
DOI: 10.1002/bip.23289

DNA-Encoded Combinatorial Library of Macrocyclic Peptoids

Min Hyeon Shin, Kang Ju Lee and Hyun-Suk Lim

Bioconjugate Chem., 2019, 30, 2931
DOI: 10.1021/acs.bioconjchem.9b00628

Solid-Phase Synthesis and Circular Dichroism Study of β-ABpeptoids

Ganesh A. Sable, Kang Ju Lee and Hyun-Suk Lim

Molecules, 2019, 24, 178
DOI: 10.3390/molecules24010178

Peptoids and Polypeptoids at the Frontier of Supra- and Macromolecular Engineering

Niklas Gangloff, Juliane Ulbricht, Thomas Lorson, Helmut Schlaad and Robert Luxenhofer

Chem. Rev., 2016, 116, 1753
DOI: 10.1021/acs.chemrev.5b00201

Submonomer Strategy toward Divergent Solid-Phase Synthesis of α-ABpeptoids

Ganesh A. Sable, Kang Ju Lee, Min-Kyung Shin and Hyun-Suk Lim

Org. Lett., 2018, 20, 2526
DOI: 10.1021/acs.orglett.8b00661

Strategies to Control the Cis‐Trans Isomerization of Peptoid Amide Bonds

Debajit Kalita, Biswajit Sahariah, Surya Pravo Mookerjee and Bani Kanta Sarma

Chemistry An Asian Journal, 2022, 17
DOI: 10.1002/asia.202200149

Uprising Unconventional Nanobiomaterials: Peptoid Nanosheets as a Multi‐Modular Platform for Advanced Biological Studies

Gustavo Carretero, Hettikankanamge Kalani Samarasekara, Alessia Battigelli and Biljana Mojsoska

Small, 2025, 21
DOI: 10.1002/smll.202406128

Design, Synthesis, Assembly, and Engineering of Peptoid Nanosheets

Ellen J. Robertson, Alessia Battigelli, Caroline Proulx, Ranjan V. Mannige, Thomas K. Haxton, Lisa Yun, Stephen Whitelam and Ronald N. Zuckermann

Acc. Chem. Res., 2016, 49, 379
DOI: 10.1021/acs.accounts.5b00439

A Facile Strategy for the Construction of Cyclic Peptoids under Microwave Irradiation through a Simple Substitution Reaction

Prathap Jeya Kaniraj and G. Maayan

Org. Lett., 2015, 17, 2110
DOI: 10.1021/acs.orglett.5b00696