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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
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    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.

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