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Title: Stereochemistry of polypeptoid chain configurations

Authors:
ORCiD logo [1];  [2];  [3];  [4];  [5];  [4]; ORCiD logo [5]
  1. Department of ChemistryUniversity of California Irvine California, Department of Chemical Engineering &, Materials ScienceUniversity of California Irvine California
  2. Center for Genomics and Systems BiologyNew York University Abu Dhabi Abu Dhabi United Arab Emirates
  3. Martin A Fisher School of PhysicsBrandeis University Waltham Massachusetts, Molecular FoundryLawrence Berkeley National Laboratory Berkeley California
  4. Department of ChemistryNew York University New York New York
  5. Molecular FoundryLawrence Berkeley National Laboratory Berkeley California
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1498162
Grant/Contract Number:  
DE‐AC02‐05CH11231
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Biopolymers
Additional Journal Information:
Journal Name: Biopolymers Journal Volume: 110 Journal Issue: 6; Journal ID: ISSN 0006-3525
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
United States
Language:
English

Citation Formats

Spencer, Ryan K., Butterfoss, Glenn L., Edison, John R., Eastwood, James R., Whitelam, Stephen, Kirshenbaum, Kent, and Zuckermann, Ronald N. Stereochemistry of polypeptoid chain configurations. United States: N. p., 2019. Web. doi:10.1002/bip.23266.
Spencer, Ryan K., Butterfoss, Glenn L., Edison, John R., Eastwood, James R., Whitelam, Stephen, Kirshenbaum, Kent, & Zuckermann, Ronald N. Stereochemistry of polypeptoid chain configurations. United States. doi:https://doi.org/10.1002/bip.23266
Spencer, Ryan K., Butterfoss, Glenn L., Edison, John R., Eastwood, James R., Whitelam, Stephen, Kirshenbaum, Kent, and Zuckermann, Ronald N. Tue . "Stereochemistry of polypeptoid chain configurations". United States. doi:https://doi.org/10.1002/bip.23266.
@article{osti_1498162,
title = {Stereochemistry of polypeptoid chain configurations},
author = {Spencer, Ryan K. and Butterfoss, Glenn L. and Edison, John R. and Eastwood, James R. and Whitelam, Stephen and Kirshenbaum, Kent and Zuckermann, Ronald N.},
abstractNote = {},
doi = {10.1002/bip.23266},
journal = {Biopolymers},
number = 6,
volume = 110,
place = {United States},
year = {2019},
month = {3}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: https://doi.org/10.1002/bip.23266

Citation Metrics:
Cited by: 3 works
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Works referenced in this record:

A fresh look at the Ramachandran plot and the occurrence of standard structures in proteins
journal, January 2010

  • Hollingsworth, Scott A.; Karplus, P. Andrew
  • BioMolecular Concepts, Vol. 1, Issue 3-4
  • DOI: 10.1515/bmc.2010.022

Stereochemistry of polypeptide chain configurations
journal, July 1963


Weak backbone CH OC and side chain tBu tBu London interactions help promote helix folding of achiral NtBu peptoids
journal, January 2016

  • Angelici, G.; Bhattacharjee, N.; Roy, O.
  • Chemical Communications, Vol. 52, Issue 24
  • DOI: 10.1039/C6CC00375C

A Peptoid Square Helix via Synergistic Control of Backbone Dihedral Angles
journal, June 2017

  • Gorske, Benjamin C.; Mumford, Emily M.; Gerrity, Charles G.
  • Journal of the American Chemical Society, Vol. 139, Issue 24
  • DOI: 10.1021/jacs.7b02319

Local and Tunable n→π* Interactions Regulate Amide Isomerism in the Peptoid Backbone
journal, July 2007

  • Gorske, Benjamin C.; Bastian, Brent L.; Geske, Grant D.
  • Journal of the American Chemical Society, Vol. 129, Issue 29
  • DOI: 10.1021/ja071310l

Peptoid Oligomers with α-Chiral, Aromatic Side Chains:  Sequence Requirements for the Formation of Stable Peptoid Helices
journal, July 2001

  • Wu, Cindy W.; Sanborn, Tracy J.; Huang, Kai
  • Journal of the American Chemical Society, Vol. 123, Issue 28
  • DOI: 10.1021/ja003154n

MolProbity : all-atom structure validation for macromolecular crystallography
journal, December 2009

  • Chen, Vincent B.; Arendall, W. Bryan; Headd, Jeffrey J.
  • Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 1
  • DOI: 10.1107/S0907444909042073

Tandem Incorporation of Enantiomeric Residues Engenders Discrete Peptoid Structures
journal, May 2016


Oligo( N- aryl glycines): A New Twist on Structured Peptoids
journal, December 2008

  • Shah, Neel H.; Butterfoss, Glenn L.; Nguyen, Khanh
  • Journal of the American Chemical Society, Vol. 130, Issue 49
  • DOI: 10.1021/ja804580n

Universal Relationship between Molecular Structure and Crystal Structure in Peptoid Polymers and Prevalence of the cis Backbone Conformation
journal, January 2018

  • Greer, Douglas R.; Stolberg, Michael A.; Kundu, Joyjit
  • Journal of the American Chemical Society, Vol. 140, Issue 2
  • DOI: 10.1021/jacs.7b11891

Synthesis, structures, and properties of nine-, twelve-, and eighteen-membered N-benzyloxyethyl cyclic α-peptoids
journal, January 2008

  • Maulucci, N.; Izzo, I.; Bifulco, G.
  • Chemical Communications, Issue 33
  • DOI: 10.1039/b806508j

Ring size effect on the solid state assembly of propargyl substituted hexa- and octacyclic peptoids
journal, January 2016

  • Tedesco, Consiglia; Meli, Alessandra; Macedi, Eleonora
  • CrystEngComm, Vol. 18, Issue 46
  • DOI: 10.1039/C6CE01800A

Peptoid nanotubes: an oligomer macrocycle that reversibly sequesters water via single-crystal-to-single-crystal transformations
journal, January 2013

  • Vollrath, Sidonie B. L.; Hu, Chunhua; Bräse, Stefan
  • Chemical Communications, Vol. 49, Issue 23
  • DOI: 10.1039/c3cc37163h

Conformations of peptoids in nanosheets result from the interplay of backbone energetics and intermolecular interactions
journal, May 2018

  • Edison, John R.; Spencer, Ryan K.; Butterfoss, Glenn L.
  • Proceedings of the National Academy of Sciences, Vol. 115, Issue 22
  • DOI: 10.1073/pnas.1800397115

Sequence-specific polypeptoids: A diverse family of heteropolymers with stable secondary structure
journal, April 1998

  • Kirshenbaum, K.; Barron, A. E.; Goldsmith, R. A.
  • Proceedings of the National Academy of Sciences, Vol. 95, Issue 8
  • DOI: 10.1073/pnas.95.8.4303

A Preliminary Survey of the Peptoid Folding Landscape
journal, November 2009

  • Butterfoss, Glenn L.; Renfrew, P. Douglas; Kuhlman, Brian
  • Journal of the American Chemical Society, Vol. 131, Issue 46
  • DOI: 10.1021/ja905267k

A bio-inspired approach to ligand design: folding single-chain peptoids to chelate a multimetallic cluster
journal, January 2018

  • Nguyen, Andy I.; Spencer, Ryan K.; Anderson, Christopher L.
  • Chemical Science, Vol. 9, Issue 47
  • DOI: 10.1039/C8SC04240C

NMR determination of the major solution conformation of a peptoid pentamer with chiral side chains
journal, April 1998

  • Armand, P.; Kirshenbaum, K.; Goldsmith, R. A.
  • Proceedings of the National Academy of Sciences, Vol. 95, Issue 8
  • DOI: 10.1073/pnas.95.8.4309

Crystallography Open Database (COD): an open-access collection of crystal structures and platform for world-wide collaboration
journal, November 2011

  • Gražulis, Saulius; Daškevič, Adriana; Merkys, Andrius
  • Nucleic Acids Research, Vol. 40, Issue D1
  • DOI: 10.1093/nar/gkr900

Peptoid Atropisomers
journal, July 2011

  • Paul, Bishwajit; Butterfoss, Glenn L.; Boswell, Mikki G.
  • Journal of the American Chemical Society, Vol. 133, Issue 28
  • DOI: 10.1021/ja2028684

Cyclic Peptoids
journal, March 2007

  • Shin, Sung Bin Y.; Yoo, Barney; Todaro, Louis J.
  • Journal of the American Chemical Society, Vol. 129, Issue 11
  • DOI: 10.1021/ja066960o

Effects of Thionation and Fluorination on Cis–Trans Isomerization in Tertiary Amides: An Investigation of N -Alkylglycine (Peptoid) Rotamers
journal, March 2015

  • Engel-Andreasen, Jens; Wich, Kathrine; Laursen, Jonas S.
  • The Journal of Organic Chemistry, Vol. 80, Issue 11
  • DOI: 10.1021/acs.joc.5b00048

N -Naphthyl Peptoid Foldamers Exhibiting Atropisomerism
journal, January 2012

  • Paul, Bishwajit; Butterfoss, Glenn L.; Boswell, Mikki G.
  • Organic Letters, Vol. 14, Issue 3
  • DOI: 10.1021/ol203452f

Construction of Peptoids with All Trans -Amide Backbones and Peptoid Reverse Turns via the Tactical Incorporation of N -Aryl Side Chains Capable of Hydrogen Bonding
journal, September 2010

  • Stringer, Joseph R.; Crapster, J. Aaron; Guzei, Ilia A.
  • The Journal of Organic Chemistry, Vol. 75, Issue 18
  • DOI: 10.1021/jo101075a

Insights into Peptoid Helix Folding Cooperativity from an Improved Backbone Potential
journal, December 2015

  • Mukherjee, Sudipto; Zhou, Guangfeng; Michel, Chris
  • The Journal of Physical Chemistry B, Vol. 119, Issue 50
  • DOI: 10.1021/acs.jpcb.5b09625

Sequence Programmable Peptoid Polymers for Diverse Materials Applications
journal, April 2015

  • Knight, Abigail S.; Zhou, Effie Y.; Francis, Matthew B.
  • Advanced Materials, Vol. 27, Issue 38
  • DOI: 10.1002/adma.201500275

Small Head-to-Tail Macrocyclic α-Peptoids
journal, May 2014

  • Culf, Adrian S.; Čuperlović-Culf, Miroslava; Léger, Daniel A.
  • Organic Letters, Vol. 16, Issue 10
  • DOI: 10.1021/ol501102b

Evidence for cis Amide Bonds in Peptoid Nanosheets
journal, April 2018

  • Hudson, Benjamin C.; Battigelli, Alessia; Connolly, Michael D.
  • The Journal of Physical Chemistry Letters, Vol. 9, Issue 10
  • DOI: 10.1021/acs.jpclett.8b01040

Structural and Spectroscopic Studies of Peptoid Oligomers with α-Chiral Aliphatic Side Chains
journal, November 2003

  • Wu, Cindy W.; Kirshenbaum, Kent; Sanborn, Tracy J.
  • Journal of the American Chemical Society, Vol. 125, Issue 44, p. 13525-13530
  • DOI: 10.1021/ja037540r

Twice tied tight: Enforcing conformational order in bicyclic peptoid oligomers
journal, January 2012

  • Vollrath, Sidonie B. L.; Bräse, Stefan; Kirshenbaum, Kent
  • Chemical Science, Vol. 3, Issue 9
  • DOI: 10.1039/c2sc20473h

Extraordinarily Robust Polyproline Type I Peptoid Helices Generated via the Incorporation of α-Chiral Aromatic N -1-Naphthylethyl Side Chains
journal, October 2011

  • Stringer, Joseph R.; Crapster, J. Aaron; Guzei, Ilia A.
  • Journal of the American Chemical Society, Vol. 133, Issue 39
  • DOI: 10.1021/ja204755p

A Threaded Loop Conformation Adopted by a Family of Peptoid Nonamers
journal, February 2006

  • Huang, Kai; Wu, Cindy W.; Sanborn, Tracy J.
  • Journal of the American Chemical Society, Vol. 128, Issue 5
  • DOI: 10.1021/ja0574318

A Helical Polymer with a Cooperative Response to Chiral Information
journal, June 1995


The tert -Butyl Side Chain: A Powerful Means to Lock Peptoid Amide Bonds in the Cis Conformation
journal, April 2013

  • Roy, O.; Caumes, C.; Esvan, Y.
  • Organic Letters, Vol. 15, Issue 9
  • DOI: 10.1021/ol400820y

Cyclic α,β-Tetrapeptoids: Sequence-Dependent Cyclization and Conformational Preference
journal, June 2013

  • Caumes, Cécile; Fernandes, Carlos; Roy, Olivier
  • Organic Letters, Vol. 15, Issue 14
  • DOI: 10.1021/ol401478j

A Peptoid Ribbon Secondary Structure
journal, April 2013

  • Crapster, J. Aaron; Guzei, Ilia A.; Blackwell, Helen E.
  • Angewandte Chemie International Edition, Vol. 52, Issue 19
  • DOI: 10.1002/anie.201208630

Peptoids and Polypeptoids at the Frontier of Supra- and Macromolecular Engineering
journal, December 2015


Structural Effects of Proline Substitution and Metal Binding on Hexameric Cyclic Peptoids
journal, January 2013

  • Izzo, Irene; Ianniello, Graziella; De Cola, Chiara
  • Organic Letters, Vol. 15, Issue 3
  • DOI: 10.1021/ol3034143