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Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

  • Matteo Panza
    Matteo Panza
    Department of Chemistry and Biochemistry, University of Missouri−St. Louis, One University Boulevard, St. Louis, Missouri 63121, United States
    More by Matteo Panza
  • Salvatore G. Pistorio
    Salvatore G. Pistorio
    Department of Chemistry and Biochemistry, University of Missouri−St. Louis, One University Boulevard, St. Louis, Missouri 63121, United States
  • Keith J. Stine
    Keith J. Stine
    Department of Chemistry and Biochemistry, University of Missouri−St. Louis, One University Boulevard, St. Louis, Missouri 63121, United States
  • , and 
  • Alexei V. Demchenko*
    Alexei V. Demchenko
    Department of Chemistry and Biochemistry, University of Missouri−St. Louis, One University Boulevard, St. Louis, Missouri 63121, United States
    *E-mail: [email protected]
Cite this: Chem. Rev. 2018, 118, 17, 8105–8150
Publication Date (Web):June 28, 2018
https://doi.org/10.1021/acs.chemrev.8b00051
Copyright © 2018 American Chemical Society

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    Abstract

    Abstract Image

    Advances in carbohydrate chemistry have certainly made common oligosaccharides much more accessible. However, many current methods still rely heavily upon specialized knowledge of carbohydrate chemistry. The application of automated technologies to chemical and life science applications such as genomics and proteomics represents a vibrant field. These automated technologies also present opportunities for their application to organic synthesis, including that of the synthesis of oligosaccharides. However, application of automated methods to the synthesis of carbohydrates is an underdeveloped area as compared to other classes of biomolecules. The overarching goal of this review article is to present the advances that have been made at the interface of carbohydrate chemistry and automated technology.

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    2. Hsin-Kai Tseng, Hung-Kai Wang, Chun-Yen Wu, Chi-Kung Ni, Chun-Cheng Lin. Exploring Regioselective Fucosylation Catalyzed by Bacterial Glycosyltransferases through Substrate Promiscuity and Acceptor-Mediated Glycosylation. ACS Catalysis 2023, 13 (16) , 10661-10671. https://doi.org/10.1021/acscatal.3c01563
    3. Xavier S. Streety, Jennifer C. Obike, Steven D. Townsend. A Hitchhiker’s Guide to Problem Selection in Carbohydrate Synthesis. ACS Central Science 2023, 9 (7) , 1285-1296. https://doi.org/10.1021/acscentsci.3c00507
    4. Benjamin Bouvier. Substituted Oligosaccharides as Protein Mimics: Deep Learning Free Energy Landscapes. Journal of Chemical Information and Modeling 2023, Article ASAP.
    5. Koji Morimoto, Kana Yanase, Tetsuya Kajimoto, Yasuyuki Kita. Metal-Free Synthesis of Acyl Glycosides and Application to Oligosaccharide Synthesis. Organic Letters 2022, 24 (49) , 9028-9032. https://doi.org/10.1021/acs.orglett.2c03661
    6. Bo Pang, Hao Wang, Hao Huang, Lizhi Liao, Yang Wang, Miao Wang, Guocheng Du, Zhen Kang. Enzymatic Production of Low-Molecular-Weight Hyaluronan and Its Oligosaccharides: A Review and Prospects. Journal of Agricultural and Food Chemistry 2022, 70 (44) , 14129-14139. https://doi.org/10.1021/acs.jafc.2c05709
    7. Yuxin Ma, Qiong Jiang, Xiufang Wang, Guozhi Xiao. Total Synthesis of Cordyceps militaris Glycans via Stereoselective Orthogonal One-Pot Glycosylation and α-Glycosylation Strategies. Organic Letters 2022, 24 (43) , 7950-7954. https://doi.org/10.1021/acs.orglett.2c03081
    8. Alexandra Tsouka, Pietro Dallabernardina, Marco Mende, Eric T. Sletten, Sabrina Leichnitz, Klaus Bienert, Kim Le Mai Hoang, Peter H. Seeberger, Felix F. Loeffler. VaporSPOT: Parallel Synthesis of Oligosaccharides on Membranes. Journal of the American Chemical Society 2022, 144 (43) , 19832-19837. https://doi.org/10.1021/jacs.2c07285
    9. Yong Wu, Yunyan Qiu, Yuanning Feng, J. Fraser Stoddart. Automating Glycan Assembly in Solution. ACS Central Science 2022, 8 (10) , 1369-1372. https://doi.org/10.1021/acscentsci.2c01043
    10. Linda Del Bino, Kitt Emilie Østerlid, Dung-Yeh Wu, Francesca Nonne, Maria Rosaria Romano, Jeroen Codée, Roberto Adamo. Synthetic Glycans to Improve Current Glycoconjugate Vaccines and Fight Antimicrobial Resistance. Chemical Reviews 2022, 122 (20) , 15672-15716. https://doi.org/10.1021/acs.chemrev.2c00021
    11. Suman Ghosh, Rajesh Chakrabortty, Shailendra Kumar, Aniruddha Das, Venkataraman Ganesh. Copper-Catalyzed Protoboration of 1,3-Diynes as a Platform for Iterative Functionalization. ACS Catalysis 2022, 12 (19) , 11660-11666. https://doi.org/10.1021/acscatal.2c03861
    12. Robin Jeanneret, Carlo Walz, Maarten van Meerbeek, Sarah Coppock, M. Carmen Galan. AuCl3-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives. Organic Letters 2022, 24 (34) , 6304-6309. https://doi.org/10.1021/acs.orglett.2c02530
    13. Scott A. Geringer, Gustavo A. Kashiwagi, Alexei V. Demchenko. Broadening the Scope of the Reverse Orthogonal Strategy for Oligosaccharide Synthesis. The Journal of Organic Chemistry 2022, 87 (15) , 9887-9895. https://doi.org/10.1021/acs.joc.2c00905
    14. Yashapal Singh, Scott A. Geringer, Alexei V. Demchenko. Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century. Chemical Reviews 2022, 122 (13) , 11701-11758. https://doi.org/10.1021/acs.chemrev.2c00029
    15. Niteshlal Kasdekar, Gulab Walke, Kshitij Deshpande, Srinivas Hotha. Glycosyl Vinylogous Carbonates as Glycosyl Donors by Metal-Free Activation. The Journal of Organic Chemistry 2022, 87 (9) , 5472-5484. https://doi.org/10.1021/acs.joc.1c02427
    16. Pan Zhang, Yingying Zhu, Zeyu Li, Wenli Zhang, Wanmeng Mu. Recent Advances on Lacto-N-neotetraose, a Commercially Added Human Milk Oligosaccharide in Infant Formula. Journal of Agricultural and Food Chemistry 2022, 70 (15) , 4534-4547. https://doi.org/10.1021/acs.jafc.2c01101
    17. Javed, Ashwani Tiwari, Zanjila Azeem, Pintu Kumar Mandal. 4,5-Dioxo-imidazolinium Cation-Promoted α-Selective Dehydrative Glycosylation of 2-Deoxy- and 2,6-Dideoxy Sugars. The Journal of Organic Chemistry 2022, 87 (5) , 3718-3729. https://doi.org/10.1021/acs.joc.1c02650
    18. Qing Zhang, Shuaishuai Wang, Zhonghua Li, Yi Lasanajak, Lei Li, Xuezheng Song. Regeneration of Free Reducing Glycans from Reductive Amination-Tagged Glycans by Oxone. The Journal of Organic Chemistry 2022, 87 (5) , 3736-3740. https://doi.org/10.1021/acs.joc.1c02709
    19. Welday Desta Weldu, Cheng-Chung Wang. Rationalizing the Stereoelectronic Influence of Interglycosidic Bond Conformations on the Reactivity of 1,4-O-Linked Disaccharide Donors. The Journal of Organic Chemistry 2021, 86 (24) , 17906-17917. https://doi.org/10.1021/acs.joc.1c02207
    20. Rui Yang, Haiqing He, Zixi Chen, Yingying Huang, Guozhi Xiao. A One-Pot Synthesis of Glycans and Nucleosides Based on ortho-(1-Phenylvinyl)benzyl Glycosides. Organic Letters 2021, 23 (21) , 8257-8261. https://doi.org/10.1021/acs.orglett.1c02998
    21. Lu Su, Yingle Feng, Kongchang Wei, Xuyang Xu, Rongying Liu, Guosong Chen. Carbohydrate-Based Macromolecular Biomaterials. Chemical Reviews 2021, 121 (18) , 10950-11029. https://doi.org/10.1021/acs.chemrev.0c01338
    22. Siai Zhou, Xuemei Zhong, Aoxin Guo, Qian Xiao, Jiaming Ao, Wanmeng Zhu, Hui Cai, Akihiro Ishiwata, Yukishige Ito, Xue-Wei Liu, Feiqing Ding. ZnI2-Directed Stereocontrolled α-Glucosylation. Organic Letters 2021, 23 (17) , 6841-6845. https://doi.org/10.1021/acs.orglett.1c02405
    23. Tong Li, Tianlu Li, Haoru Zhuang, Fengshan Wang, Richard R. Schmidt, Peng Peng. O-Glycosyl Trichloroacetimidates as Glycosyl Donors and Platinum(IV) Chloride as a Dual Catalyst Permitting Stereo- and Regioselective Glycosidations. ACS Catalysis 2021, 11 (16) , 10279-10287. https://doi.org/10.1021/acscatal.1c02256
    24. Rongkun Liu, Qingting Hua, Qixin Lou, Jiazhe Wang, Xiaona Li, Zhi Ma, You Yang. NIS/TMSOTf-Promoted Glycosidation of Glycosyl ortho-Hexynylbenzoates for Versatile Synthesis of O-Glycosides and Nucleosides. The Journal of Organic Chemistry 2021, 86 (6) , 4763-4778. https://doi.org/10.1021/acs.joc.1c00151
    25. Alexander Seitz, Raffael C. Wende, Emily Roesner, Dominik Niedek, Christopher Topp, Avene C. Colgan, Eoghan M. McGarrigle, Peter R. Schreiner. Site-Selective Acylation of Pyranosides with Oligopeptide Catalysts. The Journal of Organic Chemistry 2021, 86 (5) , 3907-3922. https://doi.org/10.1021/acs.joc.0c02772
    26. Yu-Ting Huang, Yi-Chia Su, Hsin-Ru Wu, Hsin-Hui Huang, Eugene C. Lin, Teng-Wei Tsai, Hsien-Wei Tseng, Jia-Lin Fang, Ching-Ching Yu. Sulfo-Fluorous Tagging Strategy for Site-Selective Enzymatic Glycosylation of para-Human Milk Oligosaccharides. ACS Catalysis 2021, 11 (5) , 2631-2643. https://doi.org/10.1021/acscatal.0c04934
    27. Shangshang Sun, Xinlei Wei, Xigui Zhou, Chun You. Construction of an Artificial In Vitro Synthetic Enzymatic Platform for Upgrading Low-Cost Starch to Value-Added Disaccharides. Journal of Agricultural and Food Chemistry 2021, 69 (1) , 302-314. https://doi.org/10.1021/acs.jafc.0c06936
    28. Chun-Wei Chang, Mei-Huei Lin, Chia-Hui Wu, Tsun-Yi Chiang, Cheng-Chung Wang. Mapping Mechanisms in Glycosylation Reactions with Donor Reactivity: Avoiding Generation of Side Products. The Journal of Organic Chemistry 2020, 85 (24) , 15945-15963. https://doi.org/10.1021/acs.joc.0c01313
    29. Sachin S. Shivatare, Chi-Huey Wong. Synthetic Carbohydrate Chemistry and Translational Medicine. The Journal of Organic Chemistry 2020, 85 (24) , 15780-15800. https://doi.org/10.1021/acs.joc.0c01834
    30. Robin A. Jeanneret, Simon E. Johnson, M. Carmen Galan. Conformationally Constrained Glycosyl Donors as Tools to Control Glycosylation Outcomes. The Journal of Organic Chemistry 2020, 85 (24) , 15801-15826. https://doi.org/10.1021/acs.joc.0c02045
    31. Charlotte S. Teschers, Ryan Gilmour. Flow Photocleavage for Automated Glycan Assembly (AGA). Organic Process Research & Development 2020, 24 (10) , 2234-2239. https://doi.org/10.1021/acs.oprd.0c00286
    32. Cheng-Wei Cheng, Chung-Yi Wu, Wen-Lian Hsu, Chi-Huey Wong. Programmable One-Pot Synthesis of Oligosaccharides. Biochemistry 2020, 59 (34) , 3078-3088. https://doi.org/10.1021/acs.biochem.9b00613
    33. Mallory K. Kern, Nicola L. B. Pohl. Automated Solution-Phase Synthesis of S-Glycosides for the Production of Oligomannopyranoside Derivatives. Organic Letters 2020, 22 (11) , 4156-4159. https://doi.org/10.1021/acs.orglett.0c01236
    34. Girish C. Sati, Joshua L. Martin, Yishu Xu, Tanmay Malakar, Paul M. Zimmerman, John Montgomery. Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation. Journal of the American Chemical Society 2020, 142 (15) , 7235-7242. https://doi.org/10.1021/jacs.0c03165
    35. Xiong Xiao, Jing Zeng, Jing Fang, Jiuchang Sun, Ting Li, Zejin Song, Lei Cai, Qian Wan. One-Pot Relay Glycosylation. Journal of the American Chemical Society 2020, 142 (12) , 5498-5503. https://doi.org/10.1021/jacs.0c00447
    36. Theodore Tyrikos-Ergas, Giulio Fittolani, Peter H. Seeberger, Martina Delbianco. Structural Studies Using Unnatural Oligosaccharides: Toward Sugar Foldamers. Biomacromolecules 2020, 21 (1) , 18-29. https://doi.org/10.1021/acs.biomac.9b01090
    37. Jicheng Wu, Xiaolei Li, Xiaotian Qi, Xiyan Duan, Weston L. Cracraft, Ilia A. Guzei, Peng Liu, Weiping Tang. Site-Selective and Stereoselective O-Alkylation of Glycosides by Rh(II)-Catalyzed Carbenoid Insertion. Journal of the American Chemical Society 2019, 141 (50) , 19902-19910. https://doi.org/10.1021/jacs.9b11262
    38. Rongkun Liu, Xiaoqian Li, Xiaona Li, Jiazhe Wang, You Yang. Gold(I)-Catalyzed Intermolecular Rearrangement Reaction of Glycosyl Alkynoic β-Ketoesters for the Synthesis of 4-O-Glycosylated 2-Pyrones. The Journal of Organic Chemistry 2019, 84 (21) , 14141-14150. https://doi.org/10.1021/acs.joc.9b01582
    39. J. Colin Mizia, Clay S. Bennett. Reagent Controlled Direct Dehydrative Glycosylation with 2-Deoxy Sugars: Construction of the Saquayamycin Z Pentasaccharide. Organic Letters 2019, 21 (15) , 5922-5927. https://doi.org/10.1021/acs.orglett.9b02056
    40. Salvatore G. Pistorio, Scott A. Geringer, Keith J. Stine, Alexei V. Demchenko. Manual and Automated Syntheses of the N-Linked Glycoprotein Core Glycans. The Journal of Organic Chemistry 2019, 84 (11) , 6576-6588. https://doi.org/10.1021/acs.joc.8b03056
    41. Saptashwa Chakraborty, Bijoyananda Mishra, Mahesh Neralkar, Srinivas Hotha. Stable Benzylic (1-Ethynylcyclohexanyl)carbonates Protect Hydroxyl Moieties by the Synergistic Action of [Au]/[Ag] Catalytic System. The Journal of Organic Chemistry 2019, 84 (11) , 6604-6611. https://doi.org/10.1021/acs.joc.9b00016
    42. Mónica Guberman, Peter H. Seeberger. Automated Glycan Assembly: A Perspective. Journal of the American Chemical Society 2019, 141 (14) , 5581-5592. https://doi.org/10.1021/jacs.9b00638
    43. Yunqin Zhang, Guisheng Xiang, Shaojun He, Yikao Hu, Yanjun Liu, Lili Xu, Guozhi Xiao. Orthogonal One-Pot Synthesis of Oligosaccharides Based on Glycosyl ortho-Alkynylbenzoates. Organic Letters 2019, 21 (7) , 2335-2339. https://doi.org/10.1021/acs.orglett.9b00617
    44. Chunfa Xu, Charles C. J. Loh. A Multistage Halogen Bond Catalyzed Strain-Release Glycosylation Unravels New Hedgehog Signaling Inhibitors. Journal of the American Chemical Society 2019, 141 (13) , 5381-5391. https://doi.org/10.1021/jacs.9b00040
    45. Yang Yu, Soeun Gim, Dongyoon Kim, Zohar A. Arnon, Ehud Gazit, Peter H. Seeberger, Martina Delbianco. Oligosaccharides Self-Assemble and Show Intrinsic Optical Properties. Journal of the American Chemical Society 2019, 141 (12) , 4833-4838. https://doi.org/10.1021/jacs.8b11882
    46. Zhifei Hu, Yu Tang, Biao Yu. Glycosylation with 3,5-Dimethyl-4-(2′-phenylethynylphenyl)phenyl (EPP) Glycosides via a Dearomative Activation Mechanism. Journal of the American Chemical Society 2019, 141 (12) , 4806-4810. https://doi.org/10.1021/jacs.9b00210
    47. Larissa Krasnova, Chi-Huey Wong. Oligosaccharide Synthesis and Translational Innovation. Journal of the American Chemical Society 2019, 141 (9) , 3735-3754. https://doi.org/10.1021/jacs.8b11005
    48. Milandip Karak, Yohei Joh, Masahiko Suenaga, Tohru Oishi, Kohei Torikai. 1,2-trans Glycosylation via Neighboring Group Participation of 2-O-Alkoxymethyl Groups: Application to One-Pot Oligosaccharide Synthesis. Organic Letters 2019, 21 (4) , 1221-1225. https://doi.org/10.1021/acs.orglett.9b00220
    49. Sanae Izumi, Yusuke Kobayashi, Yoshiji Takemoto. Regio- and Stereoselective Synthesis of 1,2-cis-Glycosides by Anomeric O-Alkylation with Organoboron Catalysis. Organic Letters 2019, 21 (3) , 665-670. https://doi.org/10.1021/acs.orglett.8b03823
    50. Bibek Dhakal, David Crich. Synthesis and Stereocontrolled Equatorially Selective Glycosylation Reactions of a Pseudaminic Acid Donor: Importance of the Side-Chain Conformation and Regioselective Reduction of Azide Protecting Groups. Journal of the American Chemical Society 2018, 140 (44) , 15008-15015. https://doi.org/10.1021/jacs.8b09654
    51. Federica Compostella, Laura Morelli, Luigi Lay. Antibacterial Carbohydrate Vaccines. 2023, 1-56. https://doi.org/10.1002/9783527831326.ch1
    52. Xiufang Wang, Guozhi Xiao. Recent chemical synthesis of plant polysaccharides. Current Opinion in Chemical Biology 2023, 77 , 102387. https://doi.org/10.1016/j.cbpa.2023.102387
    53. Kevin M. Dorst, Göran Widmalm. NMR chemical shift prediction and structural elucidation of linker-containing oligo- and polysaccharides using the computer program CASPER. Carbohydrate Research 2023, 533 , 108937. https://doi.org/10.1016/j.carres.2023.108937
    54. Kai Philip Hussnaetter, Philip Palm, Andrij Pich, Matthias Franzreb, Erdmann Rapp, Lothar Elling. Strategies for Automated Enzymatic Glycan Synthesis (AEGS). Biotechnology Advances 2023, 67 , 108208. https://doi.org/10.1016/j.biotechadv.2023.108208
    55. Jicheng Wu, Peijing Jia, Rositha Kuniyil, Peng Liu, Weiping Tang. Dynamic Kinetic Stereoselective Glycosylation via Rh II and Chiral Phosphoric Acid‐Cocatalyzed Carbenoid Insertion to the Anomeric OH Bond for the Synthesis of Glycoconjugates. Angewandte Chemie International Edition 2023, 62 (39) https://doi.org/10.1002/anie.202307144
    56. Jicheng Wu, Peijing Jia, Rositha Kuniyil, Peng Liu, Weiping Tang. Dynamic Kinetic Stereoselective Glycosylation via Rh II and Chiral Phosphoric Acid‐Cocatalyzed Carbenoid Insertion to the Anomeric OH Bond for the Synthesis of Glycoconjugates. Angewandte Chemie 2023, 135 (39) https://doi.org/10.1002/ange.202307144
    57. Ashley E. DeYong, Jonathan C. Trinidad, Nicola L. B. Pohl. An identification method to distinguish monomeric sugar isomers on glycopeptides. The Analyst 2023, 148 (18) , 4438-4446. https://doi.org/10.1039/D3AN01036H
    58. Lianqian Wu, Zefeng Zhou, Devavrat Sathe, Junfeng Zhou, Shoshana Dym, Zhensheng Zhao, Junpeng Wang, Jia Niu. Precision native polysaccharides from living polymerization of anhydrosugars. Nature Chemistry 2023, 15 (9) , 1276-1284. https://doi.org/10.1038/s41557-023-01193-2
    59. . Synthesis of oligosaccharide libraries for systematic explorations of heparan sulfate sequence space. Nature Chemistry 2023, 1062-1063. https://doi.org/10.1038/s41557-023-01270-6
    60. Lei Wang, Alexander W. Sorum, Bo-Shun Huang, Mallory K. Kern, Guowei Su, Nitin Pawar, Xuefei Huang, Jian Liu, Nicola L. B. Pohl, Linda C. Hsieh-Wilson. Efficient platform for synthesizing comprehensive heparan sulfate oligosaccharide libraries for decoding glycosaminoglycan–protein interactions. Nature Chemistry 2023, 15 (8) , 1108-1117. https://doi.org/10.1038/s41557-023-01248-4
    61. I‐Chen Lu, Kuang‐Chun Cheng, Yi‐Fang Wang, Chia‐Wei Pan, Jan‐Siang Hung, Kwok‐Kong Tony Mong. Orthogonal Glycosylation with Phosphate Acceptors for Expeditious Synthesis of Bacterial Inner Core Oligosaccharides. Chemistry – An Asian Journal 2023, 18 (15) https://doi.org/10.1002/asia.202300424
    62. Sasilada Sirirungruang, Collin R. Barnum, Sophia N. Tang, Patrick M. Shih. Plant glycosyltransferases for expanding bioactive glycoside diversity. Natural Product Reports 2023, 40 (7) , 1170-1180. https://doi.org/10.1039/D2NP00077F
    63. Kameshwar Prasad, Ananay Sharma, Soumyaranjan Pati, Marc Taillefer, Florian Jaroschik, Srinivas Hotha. Metal Free Activation of Alkynyl Glycosyl Carbonate Donors. Advanced Synthesis & Catalysis 2023, 365 (14) , 2344-2349. https://doi.org/10.1002/adsc.202300251
    64. Yasmeen Bakhatan, Israel Alshanski, Chieh‐Kai Chan, Wei‐Chih Lo, Po‐Wei Lu, Pin‐Hsuan Liao, Cheng‐Chung Wang, Mattan Hurevich. Accelerated Solid Phase Glycan Synthesis: ASGS. Chemistry – A European Journal 2023, 29 (38) https://doi.org/10.1002/chem.202300897
    65. Rui Freitas, Andreia Peixoto, Eduardo Ferreira, Andreia Miranda, Lúcio Lara Santos, José Alexandre Ferreira. Immunomodulatory glycomedicine: Introducing next generation cancer glycovaccines. Biotechnology Advances 2023, 65 , 108144. https://doi.org/10.1016/j.biotechadv.2023.108144
    66. Baofei Hou, Teng Zhang, Huixia Yang, Xu Han, Liwei Liu, Linfei Li, Cesare Grazioli, Xu Wu, Nan Jiang, Yeliang Wang. Advances in probing single biomolecules: From DNA bases to glycans. Interdisciplinary Materials 2023, 2 (4) , 511-528. https://doi.org/10.1002/idm2.12106
    67. Ishani Lakshika Hettiarachchi, Fenglang Wu, Maria Stoica, Xiaohua Li, Jianglong Zhu. Potassium carbonate-mediated β-selective anomeric O-alkylation with primary electrophiles: Application to the synthesis of glycosphingolipids. Tetrahedron Letters 2023, 122 , 154511. https://doi.org/10.1016/j.tetlet.2023.154511
    68. Madhuri P Rao, Anu Chauhan, Lucia Pintilie, Sudheer Kumar Singh, Madhu Ganesh. Concise route to stereoselective chlorobenzene-based spiropyrrolidine oxindoles for pursuit as antitubercular agents. Journal of Chemical Sciences 2023, 135 (2) https://doi.org/10.1007/s12039-023-02144-7
    69. Xiaojuan Zhang, Peng Xu, Zhengbing Zhou, Yazhou Zhang, Biao Yu, Yugen Zhu. An Anomeric Base‐Tolerant Ester of 8‐Alkynyl ‐1‐naphthoate for Gold(I)‐Catalyzed Glycosylation Reaction. Chinese Journal of Chemistry 2023, 41 (11) , 1305-1312. https://doi.org/10.1002/cjoc.202300005
    70. Yunqin Zhang, Leilei Wang, Qingli Zhou, Zuoshan Li, Dan Li, Caixia Yin, Xiufang Wang, Guozhi Xiao. Modular Synthesis of a Tridecasaccharide Motif of Bacteroides vulgatus Lipopolysaccharides against Inflammatory Bowel Diseases through an Orthogonal One‐Pot Glycosylation Strategy. Angewandte Chemie International Edition 2023, 62 (22) https://doi.org/10.1002/anie.202301351
    71. Yunqin Zhang, Leilei Wang, Qingli Zhou, Zuoshan Li, Dan Li, Caixia Yin, Xiufang Wang, Guozhi Xiao. Modular Synthesis of a Tridecasaccharide Motif of Bacteroides vulgatus Lipopolysaccharides against Inflammatory Bowel Diseases through an Orthogonal One‐Pot Glycosylation Strategy. Angewandte Chemie 2023, 135 (22) https://doi.org/10.1002/ange.202301351
    72. Jonathan Fabian Sierra Cantor, Karine De Oliveira Vigier, Gilles Labat, Denilson Da Silva Perez, François Jérôme. Mechanocatalytic depolymerization of hemicellulose to low molecular weight oligosaccharides over an aquivion ionomer. RSC Sustainability 2023, 1 (3) , 446-453. https://doi.org/10.1039/D3SU00028A
    73. Jhih-Yi Huang, Martina Delbianco. Recent Developments in Solid-Phase Glycan Synthesis. Synthesis 2023, 55 (09) , 1337-1354. https://doi.org/10.1055/a-1938-2293
    74. Ariza Khanam, Javed, Mohan Lal, Pintu Kumar Mandal. Trichloroisocyanuric acid (TCCA): A Suitable Reagent for Direct Glycosylations of C1‐Hemiacetals with Different Nucleophiles. Asian Journal of Organic Chemistry 2023, 12 (4) https://doi.org/10.1002/ajoc.202300044
    75. Zhimin Lv, Hongyu Liu, Huifang Hao, Faiz-Ur Rahman, Yongmin Zhang. Chemical synthesis of oligosaccharides and their application in new drug research. European Journal of Medicinal Chemistry 2023, 249 , 115164. https://doi.org/10.1016/j.ejmech.2023.115164
    76. Jie Wan, Leilei Wang, Guozhi Xiao. Total Synthesis of Phellinus ribis Glycans with Immunostimulating Activities by an Orthogonal One-Pot Glycosylation Strategy. Synlett 2023, 34 (03) , 288-292. https://doi.org/10.1055/a-1969-3992
    77. Saptashwa Chakraborty, Bijoyananda Mishra, Pratim Kumar Das, Sandip Pasari, Srinivas Hotha. Synthesis of N ‐Glycosides by Silver‐Assisted Gold Catalysis. Angewandte Chemie International Edition 2023, 62 (6) https://doi.org/10.1002/anie.202214167
    78. Saptashwa Chakraborty, Bijoyananda Mishra, Pratim Kumar Das, Sandip Pasari, Srinivas Hotha. Synthesis of N ‐Glycosides by Silver‐Assisted Gold Catalysis. Angewandte Chemie 2023, 135 (6) https://doi.org/10.1002/ange.202214167
    79. Charlotte S. Teschers, Ryan Gilmour. Fluorine‐Directed Automated Mannoside Assembly. Angewandte Chemie International Edition 2023, 62 (3) https://doi.org/10.1002/anie.202213304
    80. Charlotte S. Teschers, Ryan Gilmour. Fluor‐Dirigierte Automatisierte Mannosid Assemblierung. Angewandte Chemie 2023, 135 (3) https://doi.org/10.1002/ange.202213304
    81. Yuning Liu, Yajun Huang, Ruiyu Zhu, Mohamed A. Farag, Esra Capanoglu, Chao Zhao. Structural elucidation approaches in carbohydrates: A comprehensive review on techniques and future trends. Food Chemistry 2023, 400 , 134118. https://doi.org/10.1016/j.foodchem.2022.134118
    82. Amol D. Gholap, Rushikesh P. Said, Rutuja D. Pawar, Gauri S. Ambore, Navnath T. Hatvate. Importance of carbohydrate-drug conjugates in vaccine development: A detailed review. 2023https://doi.org/10.1016/bs.coac.2023.03.002
    83. Ye Ji Kim, Hyeonsu Lee, Young Ho Rhee. Solid Phase‐Mediated Asymmetric Palladium‐Catalyzed Hydroalkoxylation of Alkoxyallene. Advanced Synthesis & Catalysis 2022, 364 (24) , 4244-4248. https://doi.org/10.1002/adsc.202201111
    84. Wenlong Yao, De-Cai Xiong, Yun Yang, Chunmei Geng, Zisen Cong, Feifei Li, Bo-Han Li, Xianjin Qin, Li-Na Wang, Wan-Ying Xue, Nengfu Yu, Hanyu Zhang, Xia Wu, Miao Liu, Xin-Shan Ye. Automated solution-phase multiplicative synthesis of complex glycans up to a 1,080-mer. Nature Synthesis 2022, 1 (11) , 854-863. https://doi.org/10.1038/s44160-022-00171-9
    85. Faranak Pooladian, Samira Escopy, Alexei V. Demchenko. Activation of Thioglycosides with Copper(II) Bromide. Molecules 2022, 27 (21) , 7354. https://doi.org/10.3390/molecules27217354
    86. Debashis Dhara, Ashis Dhara, Paul V. Murphy, Laurence A. Mulard. Protecting group principles suited to late stage functionalization and global deprotection in oligosaccharide synthesis. Carbohydrate Research 2022, 521 , 108644. https://doi.org/10.1016/j.carres.2022.108644
    87. Yasmeen Bakhatan, Dror Ben Abba Amiel, Yonatan Sukhran, Chieh-Kai Chan, Wei-Chih Lo, Po-Wei Lu, Pin-Hsuan Liao, Cheng-Chung Wang, Mattan Hurevich. Translating solution to solid phase glycosylation conditions. Chemical Communications 2022, 58 (80) , 11256-11259. https://doi.org/10.1039/D2CC03831E
    88. Yujun Kim, Ji Young Hyun, Injae Shin. Glycan microarrays from construction to applications. Chemical Society Reviews 2022, 51 (19) , 8276-8299. https://doi.org/10.1039/D2CS00452F
    89. Lei Cai, Qi Chen, Jian Guo, Zhihua Liang, Dengxian Fu, Lingkui Meng, Jing Zeng, Qian Wan. Recyclable fluorous-tag assisted two-directional oligosaccharide synthesis enabled by interrupted Pummerer reaction mediated glycosylation. Chemical Science 2022, 13 (30) , 8759-8765. https://doi.org/10.1039/D2SC01700H
    90. Shengyang Wang, You Yang, Qian Zhu, Guo-Qiang Lin, Biao Yu. Chemical synthesis of polysaccharides. Current Opinion in Chemical Biology 2022, 69 , 102154. https://doi.org/10.1016/j.cbpa.2022.102154
    91. Xiaona Li, You Yang. Automated Chemical Solid‐Phase Synthesis of Glycans. Chinese Journal of Chemistry 2022, 40 (14) , 1714-1728. https://doi.org/10.1002/cjoc.202200183
    92. Joseph O'Sullivan, Jose Muñoz-Muñoz, Graeme Turnbull, Neil Sim, Stuart Penny, Sterghios Moschos. Beyond GalNAc! Drug delivery systems comprising complex oligosaccharides for targeted use of nucleic acid therapeutics. RSC Advances 2022, 12 (32) , 20432-20446. https://doi.org/10.1039/D2RA01999J
    93. Samira Escopy, Yashapal Singh, Keith J. Stine, Alexei V. Demchenko. HPLC‐Based Automated Synthesis of Glycans in Solution. Chemistry – A European Journal 2022, 28 (39) https://doi.org/10.1002/chem.202201180
    94. Yunqin Zhang, Yanlei Hu, Shanshan Liu, Haiqing He, Roujing Sun, Gang Lu, Guozhi Xiao. Total synthesis of Lentinus giganteus glycans with antitumor activities via stereoselective α-glycosylation and orthogonal one-pot glycosylation strategies. Chemical Science 2022, 13 (26) , 7755-7764. https://doi.org/10.1039/D2SC02176E
    95. Matthew E. Griffin, Linda C. Hsieh-Wilson. Tools for mammalian glycoscience research. Cell 2022, 185 (15) , 2657-2677. https://doi.org/10.1016/j.cell.2022.06.016
    96. Hong Yan, Fen‐Er Chen. Recent Progress in Solid‐Phase Total Synthesis of Naturally Occurring Small Peptides. Advanced Synthesis & Catalysis 2022, 364 (12) , 1934-1961. https://doi.org/10.1002/adsc.202200079
    97. Mana Mohan Mukherjee, Rina Ghosh, John A. Hanover. Recent Advances in Stereoselective Chemical O-Glycosylation Reactions. Frontiers in Molecular Biosciences 2022, 9 https://doi.org/10.3389/fmolb.2022.896187
    98. Andrius Bubliauskas, Daniel J. Blair, Henry Powell‐Davies, Philip J. Kitson, Martin D. Burke, Leroy Cronin. Digitizing Chemical Synthesis in 3D Printed Reactionware. Angewandte Chemie International Edition 2022, 61 (24) https://doi.org/10.1002/anie.202116108
    99. Andrius Bubliauskas, Daniel J. Blair, Henry Powell‐Davies, Philip J. Kitson, Martin D. Burke, Leroy Cronin. Digitizing Chemical Synthesis in 3D Printed Reactionware. Angewandte Chemie 2022, 134 (24) https://doi.org/10.1002/ange.202116108
    100. Chen Zhang, Hao Zuo, Ga Young Lee, Yike Zou, Qiu-Di Dang, K. N. Houk, Dawen Niu. Halogen-bond-assisted radical activation of glycosyl donors enables mild and stereoconvergent 1,2-cis-glycosylation. Nature Chemistry 2022, 14 (6) , 686-694. https://doi.org/10.1038/s41557-022-00918-z
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