IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v14y2023i1d10.1038_s41467-023-43786-y.html
   My bibliography  Save this article

Photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors

Author

Listed:
  • Jing Zhang

    (Peking University)

  • Zhao-Xiang Luo

    (Peking University)

  • Xia Wu

    (Peking University)

  • Chen-Fei Gao

    (Peking University)

  • Peng-Yu Wang

    (Peking University)

  • Jin-Ze Chai

    (Peking University)

  • Miao Liu

    (Peking University)

  • Xin-Shan Ye

    (Peking University)

  • De-Cai Xiong

    (Peking University
    Peking University)

Abstract

Photochemical glycosylation has attracted considerable attention in carbohydrate chemistry. However, to the best of our knowledge, visible-light-promoted glycosylation via photoactive glycosyl donor has not been reported. In the study, we report a photosensitizer-free visible-light-mediated glycosylation approach using a photoactive 2-glycosyloxy tropone as the donor. This glycosylation reaction proceeds at ambient temperature to give a wide range of O-glycosides or oligosaccharides with yields up to 99%. This method is further applied in the stereoselective preparation of various functional glycosyl phosphates/phosphosaccharides, the construction of N-glycosides/nucleosides, and the late-stage glycosylation of natural products or pharmaceuticals on gram scales, and the iterative synthesis of hexasaccharide. The protocol features uncomplicated conditions, operational simplicity, wide substrate scope (58 examples), excellent compatibility with functional groups, scalability of products (7 examples), and high yields. It provides an efficient glycosylation method for accessing O/N-glycosides and glycans.

Suggested Citation

  • Jing Zhang & Zhao-Xiang Luo & Xia Wu & Chen-Fei Gao & Peng-Yu Wang & Jin-Ze Chai & Miao Liu & Xin-Shan Ye & De-Cai Xiong, 2023. "Photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
  • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-43786-y
    DOI: 10.1038/s41467-023-43786-y
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-023-43786-y
    File Function: Abstract
    Download Restriction: no

    File URL: https://libkey.io/10.1038/s41467-023-43786-y?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
    ---><---

    References listed on IDEAS

    as
    1. Qian Zhu & Zhengnan Shen & Fabrizio Chiodo & Simone Nicolardi & Antonio Molinaro & Alba Silipo & Biao Yu, 2020. "Chemical synthesis of glycans up to a 128-mer relevant to the O-antigen of Bacteroides vulgatus," Nature Communications, Nature, vol. 11(1), pages 1-7, December.
    2. Mattia Silvi & Paolo Melchiorre, 2018. "Enhancing the potential of enantioselective organocatalysis with light," Nature, Nature, vol. 554(7690), pages 41-49, February.
    3. Yong Wu & De-Cai Xiong & Si-Cong Chen & Yong-Shi Wang & Xin-Shan Ye, 2017. "Total synthesis of mycobacterial arabinogalactan containing 92 monosaccharide units," Nature Communications, Nature, vol. 8(1), pages 1-7, April.
    4. Xiaojuan Zhang & Yutong Yang & Jiahao Ding & Yun Zhao & Hongbin Zhang & Yugen Zhu, 2022. "Stereoselective gold(I)-catalyzed approach to the synthesis of complex α-glycosyl phosphosaccharides," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    5. Penghua Li & Haiqing He & Yunqin Zhang & Rui Yang & Lili Xu & Zixi Chen & Yingying Huang & Limei Bao & Guozhi Xiao, 2020. "Glycosyl ortho-(1-phenylvinyl)benzoates versatile glycosyl donors for highly efficient synthesis of both O-glycosides and nucleosides," Nature Communications, Nature, vol. 11(1), pages 1-10, December.
    Full references (including those not matched with items on IDEAS)

    Most related items

    These are the items that most often cite the same works as this one and are cited by the same works as this one.
    1. Qi Wang & Jiayi Mu & Jie Zeng & Linxi Wan & Yangyang Zhong & Qiuhong Li & Yitong Li & Huijing Wang & Fener Chen, 2023. "Additive-controlled asymmetric iodocyclization enables enantioselective access to both α- and β-nucleosides," Nature Communications, Nature, vol. 14(1), pages 1-12, December.
    2. Guodong Fan & Qingyun Wang & Jun Xu & Pengcheng Zheng & Yonggui Robin Chi, 2023. "Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles," Nature Communications, Nature, vol. 14(1), pages 1-8, December.
    3. Le Zeng & Ling Huang & Wenhai Lin & Lin-Han Jiang & Gang Han, 2023. "Red light-driven electron sacrificial agents-free photoreduction of inert aryl halides via triplet-triplet annihilation," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    4. Le Zeng & Tiexin Zhang & Renhai Liu & Wenming Tian & Kaifeng Wu & Jingyi Zhu & Zhonghe Wang & Cheng He & Jing Feng & Xiangyang Guo & Abdoulkader Ibro Douka & Chunying Duan, 2023. "Chalcogen-bridged coordination polymer for the photocatalytic activation of aryl halides," Nature Communications, Nature, vol. 14(1), pages 1-13, 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:14:y:2023:i:1:d:10.1038_s41467-023-43786-y. 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.

    If CitEc recognized a bibliographic reference but did not link an item in RePEc to it, you can help with 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.