Literature DB >> 30957356

Orthogonal Halogen-Bonding-Driven 3D Supramolecular Assembly of Right-Handed Synthetic Helical Peptides.

Peng Teng1, Geoffrey M Gray1, Mengmeng Zheng1, Sylvia Singh1, Xiaopeng Li1, Lukasz Wojtas1, Arjan van der Vaart1, Jianfeng Cai1.   

Abstract

Peptide-mediated self-assembly is a prevalent method for creating highly ordered supramolecular architectures. Herein, we report the first example of orthogonal C-X⋅⋅⋅X-C/C-X⋅⋅⋅π halogen bonding and hydrogen bonding driven crystalline architectures based on synthetic helical peptides bearing hybrids of l-sulfono-γ-AApeptides and natural amino acids. The combination of halogen bonding, intra-/intermolecular hydrogen bonding, and intermolecular hydrophobic interactions enabled novel 3D supramolecular assembly. The orthogonal halogen bonding in the supramolecular architecture exerts a novel mechanism for the self-assembly of synthetic peptide foldamers and gives new insights into molecular recognition, supramolecular design, and rational design of biomimetic structures.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  foldamers; halogen bonding; peptides; self-assembly; structure elucidation

Year:  2019        PMID： 30957356      PMCID： PMC6534470          DOI： 10.1002/anie.201903259

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  64 in total

1.  A homochiral metal-organic porous material for enantioselective separation and catalysis

Authors: 
Journal:  Nature       Date:  2000-04-27       Impact factor: 49.962

2.  Nanohedra: using symmetry to design self assembling protein cages, layers, crystals, and filaments.

Authors:  J E Padilla; C Colovos; T O Yeates
Journal:  Proc Natl Acad Sci U S A       Date:  2001-02-20       Impact factor: 11.205

3.  Origin of attraction and directionality of the pi/pi interaction: model chemistry calculations of benzene dimer interaction.

Authors:  Seiji Tsuzuki; Kazumasa Honda; Tadafumi Uchimaru; Masuhiro Mikami; Kazutoshi Tanabe
Journal:  J Am Chem Soc       Date:  2002-01-09       Impact factor: 15.419

4.  Engineering the morphology of a self-assembling protein fibre.

Authors:  Maxim G Ryadnov; Derek N Woolfson
Journal:  Nat Mater       Date:  2003-05       Impact factor: 43.841

5.  Halogen Bonding versus Hydrogen Bonding in Driving Self-Assembly Processes Perfluorocarbon-hydrocarbon self-assembly, part IX. This work was supported by MURST (Cofinanziamento '99) and EU (COST-D12-0012). We thank Dr. A. Lunghi and Dr. P. Cardillo (Stazione Sperimentale Combustibili, S. Donato Milanese, Italy) for ARC experiments. Part VIII: ref. 9.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-05-15       Impact factor: 15.336

6.  Surprisingly stable helical conformations in alpha/beta-peptides by incorporation of cis-beta-aminocyclopropane carboxylic acids.

Authors:  Silvia De Pol; Chiara Zorn; Christian D Klein; Oliver Zerbe; Oliver Reiser
Journal:  Angew Chem Int Ed Engl       Date:  2004-01-16       Impact factor: 15.336

7.  Halogen bonds in biological molecules.

Authors:  Pascal Auffinger; Franklin A Hays; Eric Westhof; P Shing Ho
Journal:  Proc Natl Acad Sci U S A       Date:  2004-11-19       Impact factor: 11.205

8.  Hydrogen storage in microporous metal-organic frameworks.

Authors:  Nathaniel L Rosi; Juergen Eckert; Mohamed Eddaoudi; David T Vodak; Jaheon Kim; Michael O'Keeffe; Omar M Yaghi
Journal:  Science       Date:  2003-05-16       Impact factor: 47.728

9.  In vivo activation of the p53 pathway by small-molecule antagonists of MDM2.

Authors:  Lyubomir T Vassilev; Binh T Vu; Bradford Graves; Daisy Carvajal; Frank Podlaski; Zoran Filipovic; Norman Kong; Ursula Kammlott; Christine Lukacs; Christian Klein; Nader Fotouhi; Emily A Liu
Journal:  Science       Date:  2004-01-02       Impact factor: 47.728

10.  Hybrid peptide design. Hydrogen bonded conformations in peptides containing the stereochemically constrained gamma-amino acid residue, gabapentin.

Authors:  Prema G Vasudev; Kuppanna Ananda; Sunanda Chatterjee; Subrayashastry Aravinda; Narayanaswamy Shamala; Padmanabhan Balaram
Journal:  J Am Chem Soc       Date:  2007-03-10       Impact factor: 15.419
View more
  11 in total

1.  Rational Design and Synthesis of Right-Handed d-Sulfono-γ-AApeptide Helical Foldamers as Potent Inhibitors of Protein-Protein Interactions.

Authors:  Peng Sang; Yan Shi; Pirada Higbee; Minghui Wang; Sami Abdulkadir; Junhao Lu; Gary Daughdrill; Jiandong Chen; Jianfeng Cai
Journal:  J Org Chem       Date:  2020-08-02       Impact factor: 4.354

2.  Aggregation-Induced Emissive and Circularly Polarized Homogeneous Sulfono-γ-AApeptide Foldamers.

Authors:  Yan Shi; Peng Sang; Guangqiang Yin; Ruixuan Gao; Xiao Liang; Robert Brzozowski; Timothy Odom; Prahathees Eswara; Youxuan Zheng; Xiaopeng Li; Jianfeng Cai
Journal:  Adv Opt Mater       Date:  2020-04-20       Impact factor: 9.926

3.  Geared Toward Applications: A Perspective on Functional Sequence-Controlled Polymers.

Authors:  Cangjie Yang; Kevin B Wu; Yu Deng; Jingsong Yuan; Jia Niu
Journal:  ACS Macro Lett       Date:  2021-01-20       Impact factor: 6.903

4.  Sulfono-γ-AApeptides as Helical Mimetics: Crystal Structures and Applications.

Authors:  Peng Sang; Yan Shi; Bo Huang; Songyi Xue; Timothy Odom; Jianfeng Cai
Journal:  Acc Chem Res       Date:  2020-09-17       Impact factor: 22.384

5.  Activation of E6AP/UBE3A-Mediated Protein Ubiquitination and Degradation Pathways by a Cyclic γ-AA Peptide.

Authors:  Bo Huang; Li Zhou; Ruochuan Liu; Lei Wang; Songyi Xue; Yan Shi; Geon Ho Jeong; In Ho Jeong; Sihao Li; Jun Yin; Jianfeng Cai
Journal:  J Med Chem       Date:  2022-01-19       Impact factor: 7.446

6.  α/Sulfono-γ-AApeptide Hybrid Analogues of Glucagon with Enhanced Stability and Prolonged In Vivo Activity.

Authors:  Peng Sang; Hongxiang Zeng; Candy Lee; Yan Shi; Minghui Wang; Cong Pan; Lulu Wei; Chenglong Huang; Mingjun Wu; Weijun Shen; Xi Li; Jianfeng Cai
Journal:  J Med Chem       Date:  2021-09-10       Impact factor: 7.446

7.  Dimeric γ-AApeptides With Potent and Selective Antibacterial Activity.

Authors:  Minghui Wang; Ruixuan Gao; Peng Sang; Timothy Odom; Mengmeng Zheng; Yan Shi; Hai Xu; Chuanhai Cao; Jianfeng Cai
Journal:  Front Chem       Date:  2020-06-12       Impact factor: 5.221

8.  The activity of sulfono-γ-AApeptide helical foldamers that mimic GLP-1.

Authors:  Peng Sang; Zhihong Zhou; Yan Shi; Candy Lee; Zaid Amso; David Huang; Timothy Odom; Vân T B Nguyen-Tran; Weijun Shen; Jianfeng Cai
Journal:  Sci Adv       Date:  2020-05-15       Impact factor: 14.136

9.  Determination of the critical chain length for macromolecular crystallization using structurally flexible polyketones.

Authors:  Yuki Ide; Yumehiro Manabe; Yuya Inaba; Yusuke Kinoshita; Jenny Pirillo; Yuh Hijikata; Tomoki Yoneda; Kilingaru I Shivakumar; Saki Tanaka; Hitoshi Asakawa; Yasuhide Inokuma
Journal:  Chem Sci       Date:  2022-07-21       Impact factor: 9.969

10.  α-Helix-Mimicking Sulfono-γ-AApeptide Inhibitors for p53-MDM2/MDMX Protein-Protein Interactions.

Authors:  Peng Sang; Yan Shi; Junhao Lu; Lihong Chen; Leixiang Yang; Wade Borcherds; Sami Abdulkadir; Qi Li; Gary Daughdrill; Jiandong Chen; Jianfeng Cai
Journal:  J Med Chem       Date:  2020-02-03       Impact factor: 7.446
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.