IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v10y2019i1d10.1038_s41467-019-11539-5.html
   My bibliography  Save this article

Single-handed supramolecular double helix of homochiral bis(N-amidothiourea) supported by double crossed C−I···S halogen bonds

Author

Listed:
  • Xiaosheng Yan

    (Xiamen University)

  • Kunshan Zou

    (Xiamen University)

  • Jinlian Cao

    (Xiamen University)

  • Xiaorui Li

    (Xiamen University)

  • Zhixing Zhao

    (Xiamen University)

  • Zhao Li

    (Xiamen University)

  • Anan Wu

    (Xiamen University)

  • Wanzhen Liang

    (Xiamen University)

  • Yirong Mo

    (Xiamen University
    Western Michigan University)

  • Yunbao Jiang

    (Xiamen University)

Abstract

The natural DNA double helix consists of two strands of nucleotides that are held together by multiple hydrogen bonds. Here we propose to build an artificial double helix from fragments of two strands connected by covalent linkages therein, but with halogen bonding as the driving force for self-assembling the fragments to the double helix. We succeed in building such a double helix in both solution and solid state, by using a bilateral N-(p-iodobenzoyl)alanine based amidothiourea which in its folded cis-form allows double and crossed C−I···S halogen bonds that lead to right- or left-handed double helix when the two alanine residues are of the same L,L- or D,D-configuration. The double helix forms in dilute CH3CN solution of the micromolar concentration level, e.g., 5.6 μM from 2D NOESY experiments and exhibits a high thermal stability in solution up to 75 °C, suggesting cooperative and thereby strong intermolecular double crossed halogen bonding that makes the double helix stable. This is supported by the observed homochiral self-sorting in solution.

Suggested Citation

  • Xiaosheng Yan & Kunshan Zou & Jinlian Cao & Xiaorui Li & Zhixing Zhao & Zhao Li & Anan Wu & Wanzhen Liang & Yirong Mo & Yunbao Jiang, 2019. "Single-handed supramolecular double helix of homochiral bis(N-amidothiourea) supported by double crossed C−I···S halogen bonds," Nature Communications, Nature, vol. 10(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-11539-5
    DOI: 10.1038/s41467-019-11539-5
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-019-11539-5
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-019-11539-5?utm_source=ideas
    LibKey link: if access is restricted and if your library uses this service, LibKey will redirect you to where you can use your library subscription to access this item
    ---><---

    Citations

    Citations are extracted by the CitEc Project, subscribe to its RSS feed for this item.
    as


    Cited by:

    1. Yuan Wang & Dian Niu & Guanghui Ouyang & Minghua Liu, 2022. "Double helical π-aggregate nanoarchitectonics for amplified circularly polarized luminescence," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    2. Lei Xu & Li Zhou & Yan-Xiang Li & Run-Tan Gao & Zheng Chen & Na Liu & Zong-Quan Wu, 2023. "Thermo-responsive chiral micelles as recyclable organocatalyst for asymmetric Rauhut-Currier reaction in water," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    3. Debashis Mondal & Manzoor Ahmad & Bijoy Dey & Abhishek Mondal & Pinaki Talukdar, 2022. "Formation of supramolecular channels by reversible unwinding-rewinding of bis(indole) double helix via ion coordination," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    4. Xiaosheng Yan & Jinlian Cao & Huan Luo & Zhao Li & Zexing Cao & Yirong Mo & Yun-Bao Jiang, 2024. "Heterochiral coupling to bilateral β-turn structured azapeptides bearing two remote chiral centers," Nature Communications, Nature, vol. 15(1), pages 1-9, December.

    More about this item

    Statistics

    Access and download statistics

    Corrections

    All material on this site has been provided by the respective publishers and authors. You can help correct errors and omissions. When requesting a correction, please mention this item's handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-11539-5. See general information about how to correct material in RePEc.

    If you have authored this item and are not yet registered with RePEc, we encourage you to do it here. This allows to link your profile to this item. It also allows you to accept potential citations to this item that we are uncertain about.

    We have no bibliographic references for this item. You can help adding them by using this form .

    If you know of missing items citing this one, you can help us creating those links by adding the relevant references in the same way as above, for each refering item. If you are a registered author of this item, you may also want to check the "citations" tab in your RePEc Author Service profile, as there may be some citations waiting for confirmation.

    For technical questions regarding this item, or to correct its authors, title, abstract, bibliographic or download information, contact: Sonal Shukla or Springer Nature Abstracting and Indexing (email available below). General contact details of provider: http://www.nature.com .

    Please note that corrections may take a couple of weeks to filter through the various RePEc services.

    IDEAS is a RePEc service. RePEc uses bibliographic data supplied by the respective publishers.