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Mirror-image cyclodextrins

Nature Synthesis (2024)Cite this article

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Abstract

For over a century, naturally occurring cyclodextrins (CDs) have been investigated intensively and extensively. CDs possess inherently stable chiralities, which render them versatile players in diverse arenas of technology. Although naturally occurring CDs can be mass-produced by the enzymatic modification of amylose, their mirror-images have, however, remained inaccessible. Here we report the syntheses of three mirror-image CDs—namely, α-, β- and γ-l-CDs, which are composed of six, seven and eight α-1,4-linked l-glucopyranosyl residues, respectively. Hallmarks of their syntheses include the highly diastereoselective installations of multiple contiguous 1,2-cis l-glucopyranosidic linkages, the rapid assembly of linear oligosaccharides employing one-pot glycosylation strategies and three efficient diastereoselective cyclizations. The structures and inherent chiralities of all three synthetic l-CDs have been established unambiguously by single-crystal X-ray diffraction and induced electronic circular dichroism spectroscopy. The availability of l-CDs has enabled the elucidation of an unprecedented chiral self-sorting of a racemic modification of β-CDs in the solid state and an investigation of the chiral recognition of enantiomeric fenchone by α-l-CD. This research identifies a missing piece of the cyclodextrin jigsaw and sets the stage for scientists to explore the mirror-image world of naturally occurring CDs.

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Fig. 1: Synthesis of α-l-CD.
Fig. 2: Syntheses of β- and γ-l-CDs.
Fig. 3: Single-crystal X-ray crystallography.
Fig. 4: Single-crystal X-ray diffraction analysis of the β-d- and β-l-CD cocrystal.
Fig. 5: IECD spectroscopy.
Fig. 6: Chiral recognition.

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Data availability

All data that support the findings of this study are available in the main text and the Supplementary Information. X-Ray crystallographic data for the structures reported in this Article have been deposited at the Cambridge Crystallographic Data Centre (CCDC) under deposition numbers CCDC 2246203 (α-l-CD), 2246204 (β-l-CD), 2246205 (γ-l-CD) and 2266813 (β-d- and β-l-CD cocrystal). Copies of the data can be obtained free of charge via https://www.ccdc.cam.ac.uk/structures/. Source data are provided with this paper.

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Acknowledgements

Northwestern University (NU, J.F.S.), the University of Hong Kong (J.F.S.) and the Robert A. Welch Foundation (Y-0026 to D.W.A.) are acknowledged for financial support. This work made use of the Integrated Molecular Structure Education and Research Center (IMSERC) at NU, which receives support from the NIH (1S10OD012016-01/1S10RR019071-01A1), Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource (NSF ECCS-1542205), the State of Illinois and the International Institute for Nanotechnology (IIN). Use of resources of the Keck Biophysics Facility was supported in part by National Cancer Institute award CCSG-P30-CA060553 to the Robert H. Lurie Comprehensive Cancer Center at NU.

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Authors and Affiliations

  1. Department of Chemistry, Northwestern University, Evanston, IL, USA

    Yong Wu, Han Han, Chun Tang, Guangcheng Wu, Xuesong Li, Huang Wu, Charlotte L. Stern, Yunyan Qiu, Aspen X.-Y. Chen, Yang Jiao, Ruihua Zhang, Arthur H. G. David & J. Fraser Stoddart

  2. Department of Chemistry, The University of Hong Kong, Hong Kong SAR, China

    Yong Wu, Han Han, Chun Tang, Guangcheng Wu, Huang Wu, Aspen X.-Y. Chen, Ruihua Zhang & J. Fraser Stoddart

  3. Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX, USA

    Saba Aslani & Daniel W. Armstrong

  4. Department of Chemistry, University of Wyoming, Laramie, WY, USA

    Xuesong Li

  5. Stoddart Institute of Molecular Science, Department of Chemistry, Zhejiang University, Hangzhou, China

    Qing-Hui Guo & J. Fraser Stoddart

  6. ZJU-Hangzhou Global Scientific and Technological Innovation Center, Hangzhou, China

    Qing-Hui Guo & J. Fraser Stoddart

  7. Department of Chemistry, National University of Singapore, Singapore, Republic of Singapore

    Yunyan Qiu

  8. Laboratoire MOLTECH-Anjou, UMR CNRS 6200, Université d’Angers, Angers, France

    Arthur H. G. David

  9. Simpson Querrey Institute for BioNanotechnology, Northwestern University, Chicago, IL, USA

    J. Fraser Stoddart

  10. School of Chemistry, University of New South Wales, Sydney, New South Wales, Australia

    J. Fraser Stoddart

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Contributions

Y.W. and J.F.S. conceived the study and designed experiments. Y.W. performed research under J.F.S.’s guidance. S.A., G.W. and D.W.A. contributed to the chiral recognition experiments. H.H. conducted density functional theory calculations. C.T. contributed to the IECD spectroscopy and X-ray crystallographic analysis. C.L.S. collected and solved the X-ray diffraction data. X.L., H.W., Q.-H.G., Y.Q., A.X.-Y.C., Y.J., R.Z. and A.H.G.D. commented on the data and all authors contributed to data analysis. Y.W. and J.F.S. wrote the manuscript with input from all authors.

Corresponding author

Correspondence to J. Fraser Stoddart.

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Competing interests

Y.W. and J.F.S. have filed a patent application with Northwestern University (Innovation and New Ventures Office Reference No. NU 2024-020) based on this research. The other authors declare no competing interests.

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Nature Synthesis thanks Sophie Beeren, William Harrison, Chang-Chun Ling and Peng George Wang for their contribution to the peer review of this work. Primary handling editor: Peter Seavill.

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Publisher’s note The editorial team of Nature Synthesis declare that Alison Stoddart has had no involvement in the editorial handling of this article.

Supplementary information

Supplementary Information

Experimental Details, Supplementary Figs. 1–48 and Schemes 1–17.

Supplementary Data 1

X-ray crystallographic data for α-l-CD, CCDC 2246203.

Supplementary Data 2

X-ray crystallographic data for β-l-CD, CCDC 2246204.

Supplementary Data 3

X-ray crystallographic data for γ-l-CD, CCDC 2246205.

Supplementary Data 4

X-ray crystallographic data for β-d- and β-l-CD cocrystal, CCDC 2266813.

Source data

Source Data Fig. 5

Source data for Fig. 5.

Source Data Fig. 6

Source data for Fig. 6.

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Wu, Y., Aslani, S., Han, H. et al. Mirror-image cyclodextrins. Nat. Synth (2024). https://doi.org/10.1038/s44160-024-00495-8

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