Polypeptoid polymers: Synthesis, characterization, and properties

Chan, Brandon A.; Xuan, Sunting; Li, Ang; Simpson, Jessica M.; Sternhagen, Garrett L.; Yu, Tianyi; Darvish, Omead A.; Jiang, Naisheng; Zhang, Donghui

doi:10.1002/bip.23070

Polypeptoid polymers: Synthesis, characterization, and properties

Journal Article · 25 October 2017 · Biopolymers

DOI:https://doi.org/10.1002/bip.23070· OSTI ID:1537505

Chan, Brandon A. ^[1]; Xuan, Sunting ^[1]; Li, Ang ^[1]; Simpson, Jessica M. ^[1]; Sternhagen, Garrett L. ^[1]; Yu, Tianyi ^[1]; Darvish, Omead A. ^[1]; Jiang, Naisheng ^[1]; ^[1]

Department of Chemistry and Macromolecular Studies Group, Louisiana State University, Baton Rouge 70803 Los Angeles

Not provided.

Research Organization:: Louisiana State Univ., Baton Rouge, LA (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0012432

OSTI ID:: 1537505

Journal Information:: Biopolymers, Vol. 109, Issue 1; ISSN 0006-3525

Publisher:: Wiley

Country of Publication:: United States

Language:: English

References (115)

Cyclic Poly(α-peptoid)s and Their Block Copolymers from N-Heterocyclic Carbene-Mediated Ring-Opening Polymerizations of N-Substituted N -Carboxylanhydrides Guo, Li; Zhang, Donghui Journal of the American Chemical Society, Vol. 131, Issue 50 https://doi.org/10.1021/ja907380d	journal	December 2009
Amphiphilic Polypeptoids Serve as the Connective Glue to Transform Liposomes into Multilamellar Structures with Closely Spaced Bilayers Zhang, Yueheng; Xuan, Sunting; Owoseni, Olasehinde Langmuir, Vol. 33, Issue 11 https://doi.org/10.1021/acs.langmuir.6b04190	journal	March 2017
New amphipathic lipopeptides, 1. Synthesis and mesomorphic structures of lipopeptides with polysarcosine peptidic chains Douy, André; Gallot, Bernard Die Makromolekulare Chemie, Vol. 187, Issue 3, p. 465-483 https://doi.org/10.1002/macp.1986.021870301	journal	March 1986
On the biodegradability of polyethylene glycol, polypeptoids and poly(2-oxazoline)s Ulbricht, Juliane; Jordan, Rainer; Luxenhofer, Robert Biomaterials, Vol. 35, Issue 17 https://doi.org/10.1016/j.biomaterials.2014.02.029	journal	June 2014
Crystallization and Melting Behaviors of Cyclic and Linear Polypeptoids with Alkyl Side Chains Lee, Chang-Uk; Li, Ang; Ghale, Kushal Macromolecules, Vol. 46, Issue 20 https://doi.org/10.1021/ma401067f	journal	October 2013
Proteolytic studies of homologous peptide and N-substituted glycine peptoid oligomers Miller, Susan M.; Simon, Reyna J.; Ng, Simon Bioorganic & Medicinal Chemistry Letters, Vol. 4, Issue 22 https://doi.org/10.1016/S0960-894X(01)80691-0	journal	November 1994
Über die Isomerie der Carbäthoxyl-glycyl glycinester Leuchs, Hermann; Manasse, Wilhelm Berichte der deutschen chemischen Gesellschaft, Vol. 40, Issue 3 https://doi.org/10.1002/cber.19070400387	journal	June 1907
Comparison of the proteolytic susceptibilities of homologous L-amino acid, D-amino acid, and N-substituted glycine peptide and peptoid oligomers Miller, Susan M.; Simon, Reyna J.; Ng, Simon Drug Development Research, Vol. 35, Issue 1 https://doi.org/10.1002/ddr.430350105	journal	May 1995
Alkyne-X modification of polypeptoids Secker, Christian; Robinson, Joshua W.; Schlaad, Helmut European Polymer Journal, Vol. 62 https://doi.org/10.1016/j.eurpolymj.2014.08.028	journal	January 2015
Polypeptoids by Living Ring-Opening Polymerization of N-Substituted N-Carboxyanhydrides from Solid Supports Gangloff, Niklas; Fetsch, Corinna; Luxenhofer, Robert Macromolecular Rapid Communications, Vol. 34, Issue 12 https://doi.org/10.1002/marc.201300269	journal	May 2013
Crystallization in Sequence-Defined Peptoid Diblock Copolymers Induced by Microphase Separation Sun, Jing; Teran, Alexander A.; Liao, Xunxun Journal of the American Chemical Society, Vol. 136, Issue 5 https://doi.org/10.1021/ja412123y	journal	January 2014
Temperature-Triggered Fusion of Vesicles Composed of Right-Handed and Left-Handed Amphiphilic Helical Peptides Ueda, Motoki; Makino, Akira; Imai, Tomoya Langmuir, Vol. 27, Issue 8 https://doi.org/10.1021/la105140v	journal	April 2011
Self-Assemblies of Triskelion A ₂ B-Type Amphiphilic Polypeptide Showing pH-Responsive Morphology Transformation Uesaka, Akihiro; Ueda, Motoki; Makino, Akira Langmuir, Vol. 28, Issue 14 https://doi.org/10.1021/la3004867	journal	March 2012
Control of Crystallization and Melting Behavior in Sequence Specific Polypeptoids Rosales, Adrianne M.; Murnen, Hannah K.; Zuckermann, Ronald N. Macromolecules, Vol. 43, Issue 13 https://doi.org/10.1021/ma1002563	journal	July 2010
Tertiary amine catalyzed polymerizations of α-amino acidN-carboxyanhydrides: The role of cyclization Kricheldorf, Hans R.; Von Lossow, Colin; Schwarz, Gert Journal of Polymer Science Part A: Polymer Chemistry, Vol. 44, Issue 15 https://doi.org/10.1002/pola.21553	journal	January 2006
Cationic Polypeptoids with Optimized Molecular Characteristics toward Efficient Nonviral Gene Delivery Zhu, Lipeng; Simpson, Jessica M.; Xu, Xin ACS Applied Materials & Interfaces, Vol. 9, Issue 28 https://doi.org/10.1021/acsami.7b06031	journal	July 2017
Design, Synthesis, Assembly, and Engineering of Peptoid Nanosheets Robertson, Ellen J.; Battigelli, Alessia; Proulx, Caroline Accounts of Chemical Research, Vol. 49, Issue 3 https://doi.org/10.1021/acs.accounts.5b00439	journal	January 2016
Self-Assembly of Amphiphilic Block Copolypeptoids with C ₂ -C ₅ Side Chains in Aqueous Solution Fetsch, Corinna; Flecks, Silvana; Gieseler, Dan Macromolecular Chemistry and Physics, Vol. 216, Issue 5 https://doi.org/10.1002/macp.201400534	journal	December 2014
Copolymers ofL-proline and sarcosine: Synthesis and physical-chemical studies Fasman, G. D.; Blout, E. R. Biopolymers, Vol. 1, Issue 2 https://doi.org/10.1002/bip.360010202	journal	April 1963
Suppression of Murine IgE Responses with Amino Acid Polymer/Allergen Conjugates Moran, D. M.; Wheeler, A. W.; Henderson, D. C. International Archives of Allergy and Immunology, Vol. 81, Issue 4 https://doi.org/10.1159/000234163	journal	January 1986
Peptoid nanosheets exhibit a new secondary-structure motif Mannige, Ranjan V.; Haxton, Thomas K.; Proulx, Caroline Nature, Vol. 526, Issue 7573 https://doi.org/10.1038/nature15363	journal	October 2015
Mechanismus der NCA-Polymerisation, 3. Über die Amin katalysierte Polymerisation von Sarkosin-NCA und -NTA Kricheldorf, Hans R.; Bösinger, Klaus Die Makromolekulare Chemie, Vol. 177, Issue 5 https://doi.org/10.1002/macp.1976.021770502	journal	May 1976
Polypeptoids: A perfect match for molecular definition and macromolecular engineering? Luxenhofer, Robert; Fetsch, Corinna; Grossmann, Arlett Journal of Polymer Science Part A: Polymer Chemistry, Vol. 51, Issue 13 https://doi.org/10.1002/pola.26687	journal	April 2013
1,1,3,3-Tetramethylguanidine-Promoted Ring-Opening Polymerization of N -Butyl N -Carboxyanhydride Using Alcohol Initiators Chan, Brandon A.; Xuan, Sunting; Horton, Matthew Macromolecules, Vol. 49, Issue 6 https://doi.org/10.1021/acs.macromol.5b02520	journal	March 2016
Versatile peptide rafts for conjugate morphologies by self-assembling amphiphilic helical peptides Ueda, Motoki; Makino, Akira; Imai, Tomoya Polymer Journal, Vol. 45, Issue 5 https://doi.org/10.1038/pj.2013.4	journal	February 2013
Surface analysis of lipopeptides using X-ray photoelectron spectroscopy Gervais, M.; Douy, A.; Gallot, B. Journal of Colloid and Interface Science, Vol. 125, Issue 1 https://doi.org/10.1016/0021-9797(88)90063-X	journal	September 1988
Thermo-Induced Aggregation and Crystallization of Block Copolypeptoids in Water Secker, Christian; Völkel, Antje; Tiersch, Brigitte Macromolecules, Vol. 49, Issue 3 https://doi.org/10.1021/acs.macromol.5b02481	journal	January 2016
Über die Anhydride von α-Amino-N-carbonsäuren und die von α-Aminosäuren Leuchs, Hermann; Geiger, Walter Berichte der deutschen chemischen Gesellschaft, Vol. 41, Issue 2 https://doi.org/10.1002/cber.19080410232	journal	May 1908
Zwitterionic Ring-Opening Polymerization for the Synthesis of High Molecular Weight Cyclic Polymers Brown, Hayley A.; Waymouth, Robert M. Accounts of Chemical Research, Vol. 46, Issue 11 https://doi.org/10.1021/ar400072z	journal	June 2013
Interactions of Enzymes and a Lectin with a Chitin-Based Graft Copolymer Having Polysarcosine Side Chains Nakamura, Rikiya; Aoi, Keigo; Okada, Masahiko Macromolecular Bioscience, Vol. 4, Issue 6 https://doi.org/10.1002/mabi.200400008	journal	June 2004
Synthesis and Characterization of Cyclic Brush-Like Polymers by N -Heterocyclic Carbene-Mediated Zwitterionic Polymerization of N -Propargyl N -Carboxyanhydride and the Grafting-to Approach Lahasky, Samuel H.; Serem, Wilson K.; Guo, Li Macromolecules, Vol. 44, Issue 23 https://doi.org/10.1021/ma201948u	journal	December 2011
Synthesis and Characterization of Amphiphilic Cyclic Diblock Copolypeptoids from N -Heterocyclic Carbene-Mediated Zwitterionic Polymerization of N -Substituted N -Carboxyanhydride Lee, Chang-Uk; Smart, Thomas P.; Guo, Li Macromolecules, Vol. 44, Issue 24 https://doi.org/10.1021/ma2020936	journal	December 2011
Amphiphilic star-shaped poly(sarcosine)-block-poly(ε-caprolactone) diblock copolymers: one-pot synthesis, characterization, and solution properties Cui, Saide; Pan, Xianfu; Gebru, Hailemariam Journal of Materials Chemistry B, Vol. 5, Issue 4 https://doi.org/10.1039/C6TB02145J	journal	January 2017
Polypeptoid Materials: Current Status and Future Perspectives Zhang, Donghui; Lahasky, Samuel H.; Guo, Li Macromolecules, Vol. 45, Issue 15 https://doi.org/10.1021/ma202319g	journal	May 2012
Nanotube and Three-Way Nanotube Formation with Nonionic Amphiphilic Block Peptides Kanzaki, Tatsuya; Horikawa, Yoshiki; Makino, Akira Macromolecular Bioscience, Vol. 8, Issue 11 https://doi.org/10.1002/mabi.200800071	journal	November 2008
Tubulation on peptide vesicles by phase-separation of a binary mixture of amphiphilic right-handed and left-handed helical peptides Ueda, Motoki; Makino, Akira; Imai, Tomoya Soft Matter, Vol. 7, Issue 9 https://doi.org/10.1039/c0sm01308k	journal	January 2011
The Kinetics of the Polymerization of Carbonic Anhydrides Waley, S. G.; Watson, J. Journal of the American Chemical Society, Vol. 70, Issue 6 https://doi.org/10.1021/ja01186a524	journal	June 1948
Synthesis and characterization of thermo-responsive polypeptoid bottlebrushes Lahasky, Samuel H.; Lu, Lu; Huberty, Wayne A. Polym. Chem., Vol. 5, Issue 4 https://doi.org/10.1039/C3PY01356A	journal	January 2014
Cyclic polypeptides by thermal polymerization of α-amino acidN-carboxyanhydrides Kricheldorf, Hans R.; Lossow, Colin V.; Lomadze, Nino Journal of Polymer Science Part A: Polymer Chemistry, Vol. 46, Issue 12 https://doi.org/10.1002/pola.22742	journal	January 2008
Activation of B1a Cells in Peritoneal Cavity by T Cell-Independent Antigen Expressed on Polymeric Micelle Joo Kim, Cheol; Hara, Eri; Shimizu, Akira Journal of Pharmaceutical Sciences, Vol. 104, Issue 5 https://doi.org/10.1002/jps.24397	journal	May 2015
Synthesis and Characterization of Well-Defined PEGylated Polypeptoids as Protein-Resistant Polymers Xuan, Sunting; Gupta, Sudipta; Li, Xin Biomacromolecules, Vol. 18, Issue 3 https://doi.org/10.1021/acs.biomac.6b01824	journal	February 2017
Polypeptoid- block -polypeptide Copolymers: Synthesis, Characterization, and Application of Amphiphilic Block Copolypept(o)ides in Drug Formulations and Miniemulsion Techniques Birke, Alexander; Huesmann, David; Kelsch, Annette Biomacromolecules, Vol. 15, Issue 2 https://doi.org/10.1021/bm401542z	journal	January 2014
Transformation of peptide nanotubes into a vesicle via fusion driven by stereo-complex formation Ueda, Motoki; Makino, Akira; Imai, Tomoya Chemical Communications, Vol. 47, Issue 11 https://doi.org/10.1039/c0cc04209a	journal	January 2011
Persistence length of polyelectrolytes with precisely located charges Murnen, Hannah K.; Rosales, Adrianne M.; Dobrynin, Andrey V. Soft Matter, Vol. 9, Issue 1 https://doi.org/10.1039/C2SM26849C	journal	January 2013
Cyclic Polypeptides by Solvent-Induced Polymerizations of α-Amino Acid N -Carboxyanhydrides Kricheldorf, Hans R.; von Lossow, Colin; Schwarz, Gert Macromolecules, Vol. 38, Issue 13 https://doi.org/10.1021/ma0401368	journal	June 2005
Suppression of Murine IgE Responses with Amino Acid Polymer/Allergen Conjugates Henderson, D. C.; Wheeler, A. W.; Moran, D. M. International Archives of Allergy and Immunology, Vol. 82, Issue 2 https://doi.org/10.1159/000234188	journal	January 1987
Peptoid Oligomers with α-Chiral, Aromatic Side Chains: Effects of Chain Length on Secondary Structure Wu, Cindy W.; Sanborn, Tracy J.; Zuckermann, Ronald N. Journal of the American Chemical Society, Vol. 123, Issue 13 https://doi.org/10.1021/ja003153v	journal	April 2001
Structure-Determining Step in the Hierarchical Assembly of Peptoid Nanosheets Sanii, Babak; Haxton, Thomas K.; Olivier, Gloria K. ACS Nano, Vol. 8, Issue 11 https://doi.org/10.1021/nn505007u	journal	October 2014
PEG-Amine-Initiated Polymerization of Sarcosine N -Thiocarboxyanhydrides Toward Novel Double-Hydrophilic PEG- b -Polysarcosine Diblock Copolymers Tao, Xinfeng; Deng, Chao; Ling, Jun Macromolecular Rapid Communications, Vol. 35, Issue 9 https://doi.org/10.1002/marc.201400066	journal	March 2014
Factors Influencing in Vivo Disposition of Polymeric Micelles on Multiple Administrations Hara, Eri; Ueda, Motoki; Makino, Akira ACS Medicinal Chemistry Letters, Vol. 5, Issue 8 https://doi.org/10.1021/ml500112u	journal	June 2014
One-Pot Glovebox-Free Synthesis, Characterization, and Self-Assembly of Novel Amphiphilic Poly(Sarcosine- b -Caprolactone) Diblock Copolymers Cui, Saide; Wang, Xin; Li, Zhenjiang Macromolecular Rapid Communications, Vol. 35, Issue 22 https://doi.org/10.1002/marc.201400348	journal	October 2014
Polypeptoids with tunable cloud point temperatures synthesized from N-substituted glycine N-thiocarboxyanhydrides Tao, Xinfeng; Du, Jianwei; Wang, Youxiang Polymer Chemistry, Vol. 6, Issue 16 https://doi.org/10.1039/C5PY00191A	journal	January 2015
Molecular assembly composed of a dendrimer template and block polypeptides through stereocomplex formation Matsui, Hisato; Ueda, Motoki; Makino, Akira Chemical Communications, Vol. 48, Issue 49 https://doi.org/10.1039/c2cc30926b	journal	January 2012
Peptoid Oligomers with α-Chiral, Aromatic Side Chains: Sequence Requirements for the Formation of Stable Peptoid Helices Wu, Cindy W.; Sanborn, Tracy J.; Huang, Kai Journal of the American Chemical Society, Vol. 123, Issue 28 https://doi.org/10.1021/ja003154n	journal	July 2001
Aggregation of cyclic polypeptoids bearing zwitterionic end-groups with attractive dipole–dipole and solvophobic interactions: a study by small-angle neutron scattering and molecular dynamics simulation Du, Pu; Li, Ang; Li, Xin Physical Chemistry Chemical Physics, Vol. 19, Issue 22 https://doi.org/10.1039/C7CP01602F	journal	January 2017
Suppression of Murine IgE Responses with Amino Acid Polymer/Allergen Conjugates Cook, R. M.; Henderson, D. C.; Wheeler, A. W. International Archives of Allergy and Immunology, Vol. 80, Issue 4 https://doi.org/10.1159/000234081	journal	January 1986
Untersuchungen �ber ?-Amino-N-carbons�ureanhydride VI Wessely, F.; Riedl, K.; Tuppy, H. Monatshefte f�r Chemie, Vol. 81, Issue 6 https://doi.org/10.1007/BF00899328	journal	January 1950
The Organic Flatland-Recent Advances in Synthetic 2D Organic Layers Cai, Song-Liang; Zhang, Wei-Guang; Zuckermann, Ronald N. Advanced Materials, Vol. 27, Issue 38 https://doi.org/10.1002/adma.201500124	journal	March 2015
Synthesis and Characterization of Cleavable Core-Cross-Linked Micelles Based on Amphiphilic Block Copolypeptoids as Smart Drug Carriers Li, Ang; Zhang, Donghui Biomacromolecules, Vol. 17, Issue 3 https://doi.org/10.1021/acs.biomac.5b01561	journal	February 2016
Cylindrical Brush Polymers with Polysarcosine Side Chains: A Novel Biocompatible Carrier for Biomedical Applications Hörtz, Christian; Birke, Alexander; Kaps, Leonard Macromolecules, Vol. 48, Issue 7 https://doi.org/10.1021/ma502497x	journal	March 2015
Aqueous Self-Assembly of Purely Hydrophilic Block Copolymers into Giant Vesicles Brosnan, Sarah M.; Schlaad, Helmut; Antonietti, Markus Angewandte Chemie International Edition, Vol. 54, Issue 33 https://doi.org/10.1002/anie.201502100	journal	July 2015
Thermal Properties of Aliphatic Polypeptoids Fetsch, Corinna; Luxenhofer, Robert Polymers, Vol. 5, Issue 1 https://doi.org/10.3390/polym5010112	journal	January 2013
Polypeptoids from N -Substituted Glycine N -Carboxyanhydrides: Hydrophilic, Hydrophobic, and Amphiphilic Polymers with Poisson Distribution Fetsch, Corinna; Grossmann, Arlett; Holz, Lisa Macromolecules, Vol. 44, Issue 17 https://doi.org/10.1021/ma201015y	journal	September 2011
Highly Defined Multiblock Copolypeptoids: Pushing the Limits of Living Nucleophilic Ring-Opening Polymerization Fetsch, Corinna; Luxenhofer, Robert Macromolecular Rapid Communications, Vol. 33, Issue 19 https://doi.org/10.1002/marc.201200189	journal	June 2012
Patterned Polypeptoid Brushes: Patterned Polypeptoid Brushes Schneider, Maximilian; Tang, Zian; Richter, Marcus Macromolecular Bioscience, Vol. 16, Issue 1 https://doi.org/10.1002/mabi.201500314	journal	November 2015
Self-Assembly of Amphiphilic Block Copolypeptoids – Micelles, Worms and Polymersomes Fetsch, Corinna; Gaitzsch, Jens; Messager, Lea Scientific Reports, Vol. 6, Issue 1 https://doi.org/10.1038/srep33491	journal	September 2016
Amphiphilic Polyoxazoline- block -Polypeptoid Copolymers by Sequential One-Pot Ring-Opening Polymerizations Pan, Xianfu; Liu, Yaya; Li, Zhenjiang Macromolecular Chemistry and Physics, Vol. 218, Issue 6 https://doi.org/10.1002/macp.201600483	journal	January 2017
Secondary-Structure-Driven Self-Assembly of Reactive Polypept(o)ides: Controlling Size, Shape, and Function of Core Cross-Linked Nanostructures Klinker, Kristina; Schäfer, Olga; Huesmann, David Angewandte Chemie International Edition, Vol. 56, Issue 32 https://doi.org/10.1002/anie.201702624	journal	July 2017
A versatile polypeptoid platform based on N-allyl glycine Robinson, Joshua W.; Schlaad, Helmut Chemical Communications, Vol. 48, Issue 63 https://doi.org/10.1039/c2cc33881e	journal	January 2012
Rational design of peptide nanotubes for varying diameters and lengths Ueda, Motoki; Makino, Akira; Imai, Tomoya Journal of Peptide Science, Vol. 17, Issue 2 https://doi.org/10.1002/psc.1304	journal	October 2010
65. Stereochemical aspects of the reactions between α-N-carboxy-amino-acid anhydrides and primary and secondary bases Ballard, D. G. H.; Bamford, C. H. J. Chem. Soc., Vol. 0, Issue 0 https://doi.org/10.1039/JR9580000355	journal	January 1958
Thermally Induced Crosslinking of Poly( N -Propargyl Glycine) Secker, Christian; Brosnan, Sarah M.; Limberg, Felix R. P. Macromolecular Chemistry and Physics, Vol. 216, Issue 21 https://doi.org/10.1002/macp.201500223	journal	September 2015
Anhydro-N-Carboxy-DL-β-Phenylalanine Levy, A. L. Nature, Vol. 165, Issue 4187 https://doi.org/10.1038/165152a0	journal	January 1950
Primary Amine-Initiated Polymerizations of Alanine-NCA and Sarcosine-NCA Kricheldorf, Hans R.; von Lossow, Colin; Schwarz, Gert Macromolecular Chemistry and Physics, Vol. 205, Issue 7 https://doi.org/10.1002/macp.200400021	journal	May 2004
Thermoreversible and Injectable ABC Polypeptoid Hydrogels: Controlling the Hydrogel Properties through Molecular Design Xuan, Sunting; Lee, Chang-Uk; Chen, Cong Chemistry of Materials, Vol. 28, Issue 3 https://doi.org/10.1021/acs.chemmater.5b03528	journal	January 2016
Über N -Carbonsäure-anhydride Fuchs, Friedrich Berichte der deutschen chemischen Gesellschaft (A and B Series), Vol. 55, Issue 9 https://doi.org/10.1002/cber.19220550902	journal	October 1922
Suppression of Murine IgE Responses with Amino Acid Polymer/Allergen Conjugates Wheeler, A. W.; Henderson, D. C.; Garman, A. J. International Archives of Allergy and Immunology, Vol. 76, Issue 4 https://doi.org/10.1159/000233722	journal	January 1985
Suppression of Murine IgE Responses with Amino Acid Polymer/Allergen Conjugates Whittall, N.; Moran, D. M.; Wheeler, A. W. International Archives of Allergy and Immunology, Vol. 76, Issue 4 https://doi.org/10.1159/000233721	journal	January 1985
Thermoresponsive Poly( N -C3 glycine)s Robinson, Joshua W.; Secker, Christian; Weidner, Steffen Macromolecules, Vol. 46, Issue 3 https://doi.org/10.1021/ma302412v	journal	January 2013
Synthesis and Characterization of Helix-Coil Block Copoly(α-peptoid)s Guo, Li; Zhang, Donghui Non-Conventional Functional Block Copolymers https://doi.org/10.1021/bk-2011-1066.ch006	book	January 2011
Polypeptides and 100 Years of Chemistry of α-Amino AcidN-Carboxyanhydrides Kricheldorf, Hans R. Angewandte Chemie International Edition, Vol. 45, Issue 35 https://doi.org/10.1002/anie.200600693	journal	September 2006
Pharmacokinetic change of nanoparticulate formulation “Lactosome” on multiple administrations Hara, Eri; Makino, Akira; Kurihara, Kensuke International Immunopharmacology, Vol. 14, Issue 3 https://doi.org/10.1016/j.intimp.2012.07.011	journal	November 2012
Controlled Polymerization of N-Substituted Glycine N -Thiocarboxyanhydrides Initiated by Rare Earth Borohydrides toward Hydrophilic and Hydrophobic Polypeptoids Tao, Xinfeng; Deng, Yangwei; Shen, Zhiquan Macromolecules, Vol. 47, Issue 18 https://doi.org/10.1021/ma501131t	journal	September 2014
Directed Growth of Polymer Nanorods Using Surface-Initiated Ring-Opening Polymerization of N -Allyl N -Carboxyanhydride Lu, Lu; Lahasky, Samuel H.; Zhang, Donghui ACS Applied Materials & Interfaces, Vol. 8, Issue 6 https://doi.org/10.1021/acsami.5b11358	journal	September 2015
Unusual molecular mechanism behind the thermal response of polypeptoids in aqueous solutions Ma, Jianbo; Xuan, Sunting; Guerin, Abby C. Physical Chemistry Chemical Physics, Vol. 19, Issue 17 https://doi.org/10.1039/C6CP08536A	journal	January 2017
Chain Extension and Cyclization of Telechelic Polysarcosines Kricheldorf, Hans R.; v. Lossow, Colin; Schwarz, Gert Macromolecular Chemistry and Physics, Vol. 206, Issue 12 https://doi.org/10.1002/macp.200400509	journal	June 2005
Thermoresponsive Poly(α-peptoid)s: Tuning the Cloud Point Temperatures by Composition and Architecture Lahasky, Samuel H.; Hu, Xiaoke; Zhang, Donghui ACS Macro Letters, Vol. 1, Issue 5 https://doi.org/10.1021/mz300017y	journal	April 2012
Amidine-Mediated Zwitterionic Ring-Opening Polymerization of N -Alkyl N -Carboxyanhydride: Mechanism, Kinetics, and Architecture Elucidation Li, Ang; Lu, Lu; Li, Xin Macromolecules, Vol. 49, Issue 4 https://doi.org/10.1021/acs.macromol.5b02611	journal	February 2016
Poly(α-Peptoid)s Revisited: Synthesis, Properties, and Use as Biomaterial: Poly(α-Peptoid)s Revisited: Synthesis, Properties, and Use Secker, Christian; Brosnan, Sarah M.; Luxenhofer, Robert Macromolecular Bioscience, Vol. 15, Issue 7 https://doi.org/10.1002/mabi.201500023	journal	April 2015
Molecular weight distribution of polysarcosine obtained by NCA polymerization Sisido, Masahiko; Imanishi, Yukio; Higashimura, Toshinobu Die Makromolekulare Chemie, Vol. 178, Issue 11, p. 3107-3114 https://doi.org/10.1002/macp.1977.021781114	journal	November 1977
Lyotropic Lipo-Amino-Acids: Synthesis and Structural Study Gallot, B.; Hassan, H. Haj Molecular Crystals and Liquid Crystals Incorporating Nonlinear Optics, Vol. 170, Issue 1 https://doi.org/10.1080/00268948908047759	journal	May 1989
Polypeptoid Brushes by Surface-Initiated Polymerization of N-Substituted Glycine N -Carboxyanhydrides Schneider, Maximilian; Fetsch, Corinna; Amin, Ihsan Langmuir, Vol. 29, Issue 23 https://doi.org/10.1021/la4009174	journal	May 2013
Synthesis and Characterization of Stimuli-Responsive Star-Like Polypept(o)ides: Introducing Biodegradable PeptoStars Holm, Regina; Weber, Benjamin; Heller, Philipp Macromolecular Bioscience, Vol. 17, Issue 6 https://doi.org/10.1002/mabi.201600514	journal	February 2017
Crystallization-Driven Thermoreversible Gelation of Coil-Crystalline Cyclic and Linear Diblock Copolypeptoids Lee, Chang-Uk; Lu, Lu; Chen, Jihua ACS Macro Letters, Vol. 2, Issue 5 https://doi.org/10.1021/mz300667n	journal	April 2013
Hydroxyl Group Tolerated Polymerization of N-Substituted Glycine N -Thiocarboxyanhydride Mediated by Aminoalcohols: A Simple Way to α-Hydroxyl-ω-aminotelechelic Polypeptoids Tao, Xinfeng; Zheng, Botuo; Bai, Tianwen Macromolecules, Vol. 50, Issue 8 https://doi.org/10.1021/acs.macromol.7b00309	journal	April 2017
Shaken, Not Stirred: Collapsing a Peptoid Monolayer To Produce Free-Floating, Stable Nanosheets Sanii, Babak; Kudirka, Romas; Cho, Andrew Journal of the American Chemical Society, Vol. 133, Issue 51 https://doi.org/10.1021/ja206199d	journal	December 2011
Folding of a single-chain, information-rich polypeptoid sequence into a highly ordered nanosheet Kudirka, Romas; Tran, Helen; Sanii, Babak Biopolymers, Vol. 96, Issue 5 https://doi.org/10.1002/bip.21590	journal	January 2011
Controlled Synthesis of a Chitosan-Based Graft Copolymer Having Polysarcosine Side Chains Using the NCA Method with a Carboxylic Acid Additive Nakamura, Rikiya; Aoi, Keigo; Okada, Masahiko Macromolecular Rapid Communications, Vol. 27, Issue 20 https://doi.org/10.1002/marc.200600455	journal	October 2006
Size Control of Core–Shell-type Polymeric Micelle with a Nanometer Precision Makino, Akira; Hara, Eri; Hara, Isao Langmuir, Vol. 30, Issue 2 https://doi.org/10.1021/la404488n	journal	January 2014
Synthesis and characterization of cyclic and linear helical poly(α-peptoid)s by N-heterocyclic carbene-mediated ring-opening polymerizations of N-substituted N-carboxyanhydrides Guo, Li; Li, Jinhai; Brown, Zachary Biopolymers, Vol. 96, Issue 5 https://doi.org/10.1002/bip.21597	journal	January 2011
Sequence-specific polypeptoids: A diverse family of heteropolymers with stable secondary structure Kirshenbaum, K.; Barron, A. E.; Goldsmith, R. A. Proceedings of the National Academy of Sciences, Vol. 95, Issue 8 https://doi.org/10.1073/pnas.95.8.4303	journal	April 1998
Polypept(o)ides: Hybrid Systems Based on Polypeptides and Polypeptoids Klinker, Kristina; Barz, Matthias Macromolecular Rapid Communications, Vol. 36, Issue 22 https://doi.org/10.1002/marc.201500403	journal	September 2015
NMR determination of the major solution conformation of a peptoid pentamer with chiral side chains Armand, P.; Kirshenbaum, K.; Goldsmith, R. A. Proceedings of the National Academy of Sciences, Vol. 95, Issue 8 https://doi.org/10.1073/pnas.95.8.4309	journal	April 1998
N -Heterocyclic Carbene-Mediated Zwitterionic Polymerization of N-Substituted N -Carboxyanhydrides toward Poly(α-peptoid)s: Kinetic, Mechanism, and Architectural Control Guo, Li; Lahasky, Samuel H.; Ghale, Kushal Journal of the American Chemical Society, Vol. 134, Issue 22 https://doi.org/10.1021/ja210842b	journal	May 2012
Synthesis of Amphiphilic Block Copolypept(o)ides by Bifunctional Initiators: Making PeptoMicelles Redox Sensitive Holm, Regina; Klinker, Kristina; Weber, Benjamin Macromolecular Rapid Communications, Vol. 36, Issue 23 https://doi.org/10.1002/marc.201500402	journal	September 2015
Synthesis of a novel star-shaped dendrimer by radial-growth polymerization of sarcosineN-carboxyanhydride initiated with poly(trimethyleneimine) dendrimer Aoi, Keigo; Hatanaka, Tadashi; Tsutsumiuchi, Kaname Macromolecular Rapid Communications, Vol. 20, Issue 7 https://doi.org/10.1002/(SICI)1521-3927(19990701)20:7<378::AID-MARC378>3.0.CO;2-S	journal	July 1999
Suppressive immune response of poly-(sarcosine) chains in peptide-nanosheets in contrast to polymeric micelles: THE IMMUNE RESPONSE OF NANOPARTICLES Hara, Eri; Ueda, Motoki; Kim, Cheol Joo Journal of Peptide Science, Vol. 20, Issue 7 https://doi.org/10.1002/psc.2655	journal	May 2014
Sequence Programmable Peptoid Polymers for Diverse Materials Applications Knight, Abigail S.; Zhou, Effie Y.; Francis, Matthew B. Advanced Materials, Vol. 27, Issue 38 https://doi.org/10.1002/adma.201500275	journal	April 2015
Structure–Rheology Relationship in Nanosheet-Forming Peptoid Monolayers Robertson, Ellen J.; Nehls, Eric Michael; Zuckermann, Ronald N. Langmuir, Vol. 32, Issue 46 https://doi.org/10.1021/acs.langmuir.6b02736	journal	October 2016
Are N -substituted glycine N -thiocarboxyanhydride monomers really hard to polymerize? Tao, Xinfeng; Zheng, Botuo; Kricheldorf, Hans R. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 55, Issue 3 https://doi.org/10.1002/pola.28402	journal	October 2016
Peptoids and Polypeptoids at the Frontier of Supra- and Macromolecular Engineering Gangloff, Niklas; Ulbricht, Juliane; Lorson, Thomas Chemical Reviews, Vol. 116, Issue 4 https://doi.org/10.1021/acs.chemrev.5b00201	journal	December 2015
Proline Iminopeptidase Sarid, Sarah; Berger, Arieh; Katchalski, Ephraim Journal of Biological Chemistry, Vol. 234, Issue 7 https://doi.org/10.1016/S0021-9258(18)69918-1	journal	July 1959
Patterned Polypeptoid Brushes Schneider, Maximilian; Tang, Zian; Richter, Marcus Macromolecular Bioscience, Vol. 16, Issue 1 https://doi.org/10.1002/mabi.201670004	journal	January 2016
Self-Assembly of Amphiphilic Block Copolypeptoids - Micelles, Worms and Polymersomes Fetsch, Corinna; Gaitzsch, Jens; Messager, Lea Nature Publishing Group https://doi.org/10.5451/unibas-ep52101	text	January 2016
Shaken, Not Stirred: Collapsing a Peptoid Monolayer to Produce Free-Floating, Stable Nanosheets Sanii, Babak; Kudirka, Romas; Cho, Andrew Biophysical Journal, Vol. 102, Issue 3 https://doi.org/10.1016/j.bpj.2011.11.1481	journal	January 2012

Cited By (7)

Atomic-level engineering and imaging of polypeptoid crystal lattices Xuan, Sunting; Jiang, Xi; Spencer, Ryan K. Proceedings of the National Academy of Sciences, Vol. 116, Issue 45 https://doi.org/10.1073/pnas.1909992116	journal	October 2019
Design and preparation of organic nanomaterials using self‐assembled peptoids Battigelli, Alessia Biopolymers, Vol. 110, Issue 4 https://doi.org/10.1002/bip.23265	journal	February 2019
Linking two worlds in polymer chemistry: The influence of block uniformity and dispersity in amphiphilic block copolypeptoids on their self‐assembly Gangloff, Niklas; Höferth, Marcel; Stepanenko, Vladimir Biopolymers, Vol. 110, Issue 4 https://doi.org/10.1002/bip.23259	journal	February 2019
Thermoresponsive polysarcosine-based nanoparticles Yu, Huayang; Ingram, Nicola; Rowley, Jason V. Journal of Materials Chemistry B, Vol. 7, Issue 26 https://doi.org/10.1039/c9tb00588a	journal	January 2019
Recent advances in crystallization and self‐assembly of polypeptoid polymers Zeng, Guangjian; Qiu, Lu; Wen, Tao POLYMER CRYSTALLIZATION, Vol. 2, Issue 3 https://doi.org/10.1002/pcr2.10065	journal	June 2019
Dual‐responsive pegylated polypeptoids with tunable cloud point temperatures Fu, Xiaohui; Tian, Jiliang; Li, Zheng Biopolymers, Vol. 110, Issue 4 https://doi.org/10.1002/bip.23243	journal	December 2018
Nanosized Delivery Systems for Therapeutic Proteins: Clinically Validated Technologies and Advanced Development Strategies Moncalvo, Filippo; Martinez Espinoza, Maria Isabel; Cellesi, Francesco Frontiers in Bioengineering and Biotechnology, Vol. 8 https://doi.org/10.3389/fbioe.2020.00089	journal	February 2020

Similar Records

Polypeptoid polymers: Synthesis, characterization, and properties

Journal Article · 2017 · Biopolymers · OSTI ID:1676406

Chan, Brandon A.; Xuan, Sunting; Li, Ang; +6 more

Related Subjects

Biochemistry & Molecular Biology
Biophysics

Polypeptoid polymers: Synthesis, characterization, and properties

Citation Formats

References (115)

Cited By (7)

Similar Records

Related Subjects