ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Figure 1Loading Img

Synthesis of C-Mannosylated Glycopeptides Enabled by Ni-Catalyzed Photoreductive Cross-Coupling Reactions

  • Runyu Mao
    Runyu Mao
    The Walter and Eliza Hall Institute of Medical Research, Parkville, Victoria 3052, Australia
    Department of Medical Biology, University of Melbourne, Parkville, Victoria 3010, Australia
    More by Runyu Mao
  • Shiyi Xi
    Shiyi Xi
    The Walter and Eliza Hall Institute of Medical Research, Parkville, Victoria 3052, Australia
    Department of Medical Biology, University of Melbourne, Parkville, Victoria 3010, Australia
    More by Shiyi Xi
  • Sayali Shah
    Sayali Shah
    The Walter and Eliza Hall Institute of Medical Research, Parkville, Victoria 3052, Australia
    Department of Medical Biology, University of Melbourne, Parkville, Victoria 3010, Australia
    More by Sayali Shah
  • Michael J. Roy
    Michael J. Roy
    The Walter and Eliza Hall Institute of Medical Research, Parkville, Victoria 3052, Australia
    Department of Medical Biology, University of Melbourne, Parkville, Victoria 3010, Australia
  • Alan John
    Alan John
    The Walter and Eliza Hall Institute of Medical Research, Parkville, Victoria 3052, Australia
    Department of Medical Biology, University of Melbourne, Parkville, Victoria 3010, Australia
    More by Alan John
  • James P. Lingford
    James P. Lingford
    The Walter and Eliza Hall Institute of Medical Research, Parkville, Victoria 3052, Australia
    Department of Medical Biology, University of Melbourne, Parkville, Victoria 3010, Australia
  • Gerd Gäde
    Gerd Gäde
    Department of Biological Sciences, University of Cape Town, RSA-7700 Rondebosch, South Africa
    More by Gerd Gäde
  • Nichollas E. Scott
    Nichollas E. Scott
    Department of Microbiology and Immunology, University of Melbourne at the Peter Doherty Institute for Infection and Immunity, Parkville, Victoria 3010, Australia
  • , and 
  • Ethan D. Goddard-Borger*
    Ethan D. Goddard-Borger
    The Walter and Eliza Hall Institute of Medical Research, Parkville, Victoria 3052, Australia
    Department of Medical Biology, University of Melbourne, Parkville, Victoria 3010, Australia
    *Email: [email protected]
Cite this: J. Am. Chem. Soc. 2021, 143, 32, 12699–12707
Publication Date (Web):August 4, 2021
https://doi.org/10.1021/jacs.1c05567
Copyright © 2021 American Chemical Society

    Article Views

    6143

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (1)»

    Abstract

    Abstract Image

    The biological functions of tryptophan C-mannosylation are poorly understood, in part, due to a dearth of methods for preparing pure glycopeptides and glycoproteins with this modification. To address this issue, efficient and scalable methods are required for installing this protein modification. Here, we describe unique Ni-catalyzed cross-coupling conditions that utilize photocatalysis or a Hantzsch ester photoreductant to couple glycosyl halides with (hetero)aryl bromides, thereby enabling the α-C-mannosylation of 2-bromo-tryptophan, peptides thereof, and (hetero)aryl bromides more generally. We also report that 2-(α-d-mannopyranosyl)-L-tryptophan undergoes facile anomerization in the presence of acid: something that must be considered when preparing and handling peptides with this modification. These developments enabled the first automated solid-phase peptide syntheses of C-mannosylated glycopeptides, which we used to map the epitope of an antibody, as well as providing the first verified synthesis of Carmo-HrTH-I, a C-mannosylated insect hormone. To complement this approach, we also performed late-stage tryptophan C-mannosylation on a diverse array of peptides, demonstrating the broad scope and utility of this methodology for preparing glycopeptides.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.1c05567.

    • Experimental procedures and analytical data (PDF)

    Terms & Conditions

    Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machine-readable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 26 publications.

    1. Tayyab Gulzar, Yan-Hua Liu, Yu-Nong Xia, Wei Liu, Pengchao Liu, Dapeng Zhu, Peng Xu, Biao Yu. Synthesis of C-Oligosaccharides via Ni-Catalyzed Reductive Hydroglycosylation. Organic Letters 2024, 26 (8) , 1718-1722. https://doi.org/10.1021/acs.orglett.4c00289
    2. Xiang-Yu Ye, Guanjie Wang, Zhichao Jin, Bin Yu, Junmin Zhang, Shichao Ren, Yonggui Robin Chi. Direct Formation of Amide-Linked C-Glycosyl Amino Acids and Peptides via Photoredox/Nickel Dual Catalysis. Journal of the American Chemical Society 2024, 146 (8) , 5502-5510. https://doi.org/10.1021/jacs.3c13456
    3. Yan Xia, Yingjie Wang, Zhaolun Zhang, Tayyab Gulzar, Yuqi Lin, Jing Wang, Dapeng Zhu, Biao Yu. Synthesis of 2-Indolyl C-Glycoside Neopetrosins A and C and Congeners via Ni-Catalyzed Photoreductive Cross-Coupling. Organic Letters 2023, 25 (36) , 6741-6745. https://doi.org/10.1021/acs.orglett.3c02601
    4. Rui-Qiang Jiao, Ya-Nan Ding, Ming Li, Wei-Yu Shi, Xi Chen, Zhe Zhang, Wan-Xu Wei, Xue-Song Li, Xiao-Ping Gong, Yu-Yong Luan, Xue-Yuan Liu, Yong-Min Liang. Visible-Light-Mediated Synthesis of C-Alkyl Glycosides via Glycosyl Radical Addition and Aryl Migration. Organic Letters 2023, 25 (33) , 6099-6104. https://doi.org/10.1021/acs.orglett.3c01988
    5. Lorenzo Poletti, Alessandro Massi, Daniele Ragno, Federico Droghetti, Mirco Natali, Carmela De Risi, Olga Bortolini, Graziano Di Carmine. Modulable Photocatalyzed Strategies for the Synthesis of α-C-Glycosyl Alanine Analogues via the Giese Reaction with Dehydroalanine Derivates. Organic Letters 2023, 25 (26) , 4862-4867. https://doi.org/10.1021/acs.orglett.3c01660
    6. J. Cameron Twitty, Yun Hong, Bria Garcia, Stephanie Tsang, Jennie Liao, Danielle M. Schultz, Jennifer Hanisak, Susan L. Zultanski, Amelie Dion, Dipannita Kalyani, Mary P. Watson. Diversifying Amino Acids and Peptides via Deaminative Reductive Cross-Couplings Leveraging High-Throughput Experimentation. Journal of the American Chemical Society 2023, 145 (10) , 5684-5695. https://doi.org/10.1021/jacs.2c11451
    7. Neha Singh Chauhan, Atul Dubey, Pintu Kumar Mandal. Palladium-Catalyzed Direct C–H Glycosylation of Free (N-H) Indole and Tryptophan by Norbornene-Mediated Regioselective C–H Activation. Organic Letters 2022, 24 (39) , 7067-7071. https://doi.org/10.1021/acs.orglett.2c02537
    8. Ya-Nan Ding, Ning Li, Yan-Chong Huang, Wei-Yu Shi, Nian Zheng, Cui-Tian Wang, Yang An, Xue-Yuan Liu, Yong-Min Liang. One-Pot Stereoselective Synthesis of 2,3-Diglycosylindoles and Tryptophan-C-glycosides via Palladium-Catalyzed C–H Glycosylation of Indole and Tryptophan. Organic Letters 2022, 24 (12) , 2381-2386. https://doi.org/10.1021/acs.orglett.2c00602
    9. Cai-Yi Li, Yue Ma, Zhi-Wei Lei, Xiang-Guo Hu. Glycosyl-Radical-Based Synthesis of C-Alkyl Glycosides via Photomediated Defluorinative gem-Difluoroallylation. Organic Letters 2021, 23 (22) , 8899-8904. https://doi.org/10.1021/acs.orglett.1c03390
    10. Mengran Wang, Chao Wang, Xiuling Xie, Da Pan, Liangyu Liu, Qiao Chen, Zhixuan Li, Qi Zhang, Zhaoqing Xu. Non-classical C -saccharide linkage of dehydroalanine: synthesis of C -glycoamino acids and C -glycopeptides. Chemical Communications 2023, 59 (22) , 3305-3308. https://doi.org/10.1039/D2CC06653J
    11. Alan John, Stefanie M. Bader, Niccolay Madiedo Soler, Kharizta Wiradiputri, Swapnil Tichkule, Sean T. Smyth, Stuart A. Ralph, Aaron R. Jex, Nichollas E. Scott, Christopher J. Tonkin, Ethan D. Goddard-Borger. Conservation, abundance, glycosylation profile, and localization of the TSP protein family in Cryptosporidium parvum. Journal of Biological Chemistry 2023, 299 (3) , 103006. https://doi.org/10.1016/j.jbc.2023.103006
    12. Chao Wang, Rupeng Qi, Zhaoqing Xu. Glycosyl Radical‐Based Synthesis of C ‐Glycoamino Acids and C ‐Glycopeptides. Chemistry – A European Journal 2023, 19 https://doi.org/10.1002/chem.202203689
    13. Chen Zhang, Shi-Yang Xu, Hao Zuo, Xia Zhang, Qiu-Di Dang, Dawen Niu. Direct synthesis of unprotected aryl C-glycosides by photoredox Ni-catalysed cross-coupling. Nature Synthesis 2023, 109 https://doi.org/10.1038/s44160-022-00214-1
    14. Joël S. Bloch, Alan John, Runyu Mao, Somnath Mukherjee, Jérémy Boilevin, Rossitza N. Irobalieva, Tamis Darbre, Nichollas E. Scott, Jean-Louis Reymond, Anthony A. Kossiakoff, Ethan D. Goddard-Borger, Kaspar P. Locher. Structure, sequon recognition and mechanism of tryptophan C-mannosyltransferase. Nature Chemical Biology 2023, 21 https://doi.org/10.1038/s41589-022-01219-9
    15. Uzma Afzal, Muhammad Bilal, Muhammad Zubair, Nasir Rasool, Syed Adnan Ali Shah, Zainul Amiruddin Zakaria. Stereospecific/stereoselective nickel catalyzed reductive cross-coupling: An efficient tool for the synthesis of biological active targeted molecules. Journal of Saudi Chemical Society 2023, 27 (1) , 101589. https://doi.org/10.1016/j.jscs.2022.101589
    16. Titli Ghosh, Toshiki Nokami. Recent development of stereoselective C-glycosylation via generation of glycosyl radical. Carbohydrate Research 2022, 522 , 108677. https://doi.org/10.1016/j.carres.2022.108677
    17. Anrong Chen, Bo Yang, Zhenghong Zhou, Feng Zhu. Recent advances in transition-metal-catalyzed glycosyl cross-coupling reactions. Chem Catalysis 2022, 2 (12) , 3430-3470. https://doi.org/10.1016/j.checat.2022.10.019
    18. Sash Lopaticki, Robyn McConville, Alan John, Niall Geoghegan, Shihab Deen Mohamed, Lisa Verzier, Ryan W. J. Steel, Cindy Evelyn, Matthew T. O’Neill, Niccolay Madiedo Soler, Nichollas E. Scott, Kelly L. Rogers, Ethan D. Goddard-Borger, Justin A. Boddey. Tryptophan C-mannosylation is critical for Plasmodium falciparum transmission. Nature Communications 2022, 13 (1) https://doi.org/10.1038/s41467-022-32076-8
    19. Yi Jiang, Kai Yang, Yi Wei, Quanquan Wang, Shi‐Jun Li, Yu Lan, Ming Joo Koh. Catalytic Multicomponent Synthesis of C ‐Acyl Glycosides by Consecutive Cross‐Electrophile Couplings. Angewandte Chemie 2022, 134 (46) https://doi.org/10.1002/ange.202211043
    20. Yi Jiang, Kai Yang, Yi Wei, Quanquan Wang, Shi‐Jun Li, Yu Lan, Ming Joo Koh. Catalytic Multicomponent Synthesis of C ‐Acyl Glycosides by Consecutive Cross‐Electrophile Couplings. Angewandte Chemie International Edition 2022, 61 (46) https://doi.org/10.1002/anie.202211043
    21. Zhenbo Yuan, Changtong Zhu, Yan Zhang, Yijian Rao. Post‐Modification of Amino Acids and Peptides for the Rapid Synthesis of C ‐Glycoamino Acids and C ‐Glycopeptides. European Journal of Organic Chemistry 2022, 2022 (41) https://doi.org/10.1002/ejoc.202201036
    22. Rupeng Qi, Chao Wang, Zijian Ma, Hongying Wang, Qiao Chen, Liangyu Liu, Da Pan, Xiaoyu Ren, Rui Wang, Zhaoqing Xu. Visible‐Light‐Promoted Stereoselective C(sp 3 )−H Glycosylation for the Synthesis of C ‐Glycoamino Acids and C ‐Glycopeptides. Angewandte Chemie 2022, 134 (24) https://doi.org/10.1002/ange.202200822
    23. Rupeng Qi, Chao Wang, Zijian Ma, Hongying Wang, Qiao Chen, Liangyu Liu, Da Pan, Xiaoyu Ren, Rui Wang, Zhaoqing Xu. Visible‐Light‐Promoted Stereoselective C(sp 3 )−H Glycosylation for the Synthesis of C ‐Glycoamino Acids and C ‐Glycopeptides. Angewandte Chemie International Edition 2022, 61 (24) https://doi.org/10.1002/anie.202200822
    24. Zanjila Azeem, Pintu Kumar Mandal. Recent advances in palladium-catalyzed C(sp 3 )/C(sp 2 )–H bond functionalizations: access to C-branched glycosides. Organic & Biomolecular Chemistry 2022, 20 (2) , 264-281. https://doi.org/10.1039/D1OB02142G
    25. Midori Ikezaki, Kazuchika Nishitsuji, Ko Matsumura, Shino Manabe, Yukinao Shibukawa, Yoshinao Wada, Yukishige Ito, Yoshito Ihara. C-Mannosylated tryptophan-containing WSPW peptide binds to actinin-4 and alters E-cadherin subcellular localization in lung epithelial-like A549 cells. Biochimie 2022, 192 , 136-146. https://doi.org/10.1016/j.biochi.2021.10.007
    26. Shiho Minakata, Shino Manabe, Yoko Inai, Midori Ikezaki, Kazuchika Nishitsuji, Yukishige Ito, Yoshito Ihara. Protein C-Mannosylation and C-Mannosyl Tryptophan in Chemical Biology and Medicine. Molecules 2021, 26 (17) , 5258. https://doi.org/10.3390/molecules26175258

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect