ACS Publications. Most Trusted. Most Cited. Most Read
A Four-Component One-Pot Synthesis of α-Gal Pentasaccharide
My Activity
    Letter

    A Four-Component One-Pot Synthesis of α-Gal Pentasaccharide
    Click to copy article linkArticle link copied!

    View Author Information
    The State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd 38, Beijing 100083, China, and Department of Chemistry, University of Toledo, 2801 W. Bancroft Street, MS 602, Toledo, Ohio 43606
    Other Access OptionsSupporting Information (1)

    Organic Letters

    Cite this: Org. Lett. 2004, 6, 24, 4415–4417
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol0483246
    Published October 27, 2004
    Copyright © 2004 American Chemical Society

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    A four-component one-pot sequential synthesis of α-Gal pentasaccharide 2 with minimal protecting group manipulations in a very short period of time is described in this paper.

    Copyright © 2004 American Chemical Society

    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. Add or change your institution or let them know you’d like them to include access.

     Peking University.

     University of Toledo.

    *

     To whom correspondence should be addressed. Tel:  86-10-82801570. Fax:  86-10-62014949.

    Supporting Information Available

    Click to copy section linkSection link copied!

    Synthetic procedures and spectral data of all new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!

    This article is cited by 56 publications.

    1. Wenlong Yao, Xin-Shan Ye. Donor Preactivation-Based Glycan Assembly: from Manual to Automated Synthesis. Accounts of Chemical Research 2024, 57 (11) , 1577-1594. https://doi.org/10.1021/acs.accounts.4c00072
    2. Pablo Morrone-Pozzuto, María Laura Uhrig, Rosalia Agusti. Synthesis of Oligosaccharides Containing the S-Galp(α1 → 3)Galp Unit, Glycomimetic of the Epitope Recognized by Lytic Antibodies. The Journal of Organic Chemistry 2022, 87 (20) , 13455-13468. https://doi.org/10.1021/acs.joc.2c01059
    3. 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
    4. 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
    5. Yanxin Zhang, Han Zhang, Ying Zhao, Zhongwu Guo, Jian Gao. Efficient Strategy for α-Selective Glycosidation of d-Glucosamine and Its Application to the Synthesis of a Bacterial Capsular Polysaccharide Repeating Unit Containing Multiple α-Linked GlcNAc Residues. Organic Letters 2020, 22 (4) , 1520-1524. https://doi.org/10.1021/acs.orglett.0c00101
    6. Suvarn S. Kulkarni, Cheng-Chung Wang, Narayana Murthy Sabbavarapu, Ananda Rao Podilapu, Pin-Hsuan Liao, Shang-Cheng Hung. “One-Pot” Protection, Glycosylation, and Protection–Glycosylation Strategies of Carbohydrates. Chemical Reviews 2018, 118 (17) , 8025-8104. https://doi.org/10.1021/acs.chemrev.8b00036
    7. A. R. Vartak S. J. Sucheck . Advances in Synthetic Approaches towards Glycoantigens. 2018, 175-195. https://doi.org/10.1021/bk-2018-1290.ch008
    8. Heung Sik Hahm, Chien-Fu Liang, Chian-Hui Lai, Richard J. Fair, Frank Schuhmacher, and Peter H. Seeberger . Automated Glycan Assembly of Complex Oligosaccharides Related to Blood Group Determinants. The Journal of Organic Chemistry 2016, 81 (14) , 5866-5877. https://doi.org/10.1021/acs.joc.6b00554
    9. Ananda Rao Podilapu and Suvarn S. Kulkarni . First Synthesis of Bacillus cereus Ch HF-PS Cell Wall Trisaccharide Repeating Unit. Organic Letters 2014, 16 (16) , 4336-4339. https://doi.org/10.1021/ol5021527
    10. Jun Zhou, Liping Yang, and Wenhao Hu . Stereoselective Synthesis of a Sulfated Tetrasaccharide Corresponding to a Rare Sequence in the Galactofucan Isolated from Sargassum polycystum. The Journal of Organic Chemistry 2014, 79 (10) , 4718-4726. https://doi.org/10.1021/jo500503r
    11. Li Xia and Todd L. Lowary . Regioselective Polymethylation of α-(1 → 4)-Linked Mannopyranose Oligosaccharides. The Journal of Organic Chemistry 2013, 78 (7) , 2863-2880. https://doi.org/10.1021/jo4001299
    12. James T. Smoot and Alexei V. Demchenko. How the Arming Participating Moieties can Broaden the Scope of Chemoselective Oligosaccharide Synthesis by Allowing the Inverse Armed−Disarmed Approach. The Journal of Organic Chemistry 2008, 73 (22) , 8838-8850. https://doi.org/10.1021/jo801551r
    13. David Crich and Baolin Wu. Stereoselective Iterative One-Pot Synthesis of N-Glycolylneuraminic Acid-Containing Oligosaccharides. Organic Letters 2008, 10 (18) , 4033-4035. https://doi.org/10.1021/ol801548k
    14. Silvia Valerio, Antonello Pastore, Matteo Adinolfi and Alfonso Iadonisi. Sequential One-Pot Glycosidations Catalytically Promoted: Unprecedented Strategy in Oligosaccharide Synthesis for the Straightforward Assemblage of the Antitumor PI-88 Pentasaccharide. The Journal of Organic Chemistry 2008, 73 (12) , 4496-4503. https://doi.org/10.1021/jo8003953
    15. Stefan Oscarson, Aisling Ní Cheallaigh. Strategies in Oligosaccharide Synthesis. 2021, 1-48. https://doi.org/10.1016/B978-0-12-819475-1.00075-4
    16. Andrea Marchesi, Fabio Parmeggiani, João Louçano, Ashley P. Mattey, Kun Huang, Tanistha Gupta, Mario Salwiczek, Sabine L. Flitsch. Enzymatic Building‐Block Synthesis for Solid‐Phase Automated Glycan Assembly. Angewandte Chemie 2020, 132 (50) , 22642-22645. https://doi.org/10.1002/ange.202008067
    17. Andrea Marchesi, Fabio Parmeggiani, João Louçano, Ashley P. Mattey, Kun Huang, Tanistha Gupta, Mario Salwiczek, Sabine L. Flitsch. Enzymatic Building‐Block Synthesis for Solid‐Phase Automated Glycan Assembly. Angewandte Chemie International Edition 2020, 59 (50) , 22456-22459. https://doi.org/10.1002/anie.202008067
    18. Joicy Santamalvina dos Santos, Loyanne C. Ramos, Lucimara P. Ferreira, Vanessa Leira Campo, Lucas C.D. de Rezende, Flávio da Silva Emery, Roberto Santana da Silva. Cytotoxicity, cellular uptake, and subcellular localization of a nitrogen oxide and aminopropyl-β-lactose derivative ruthenium complex used as nitric oxide delivery agent. Nitric Oxide 2019, 86 , 38-47. https://doi.org/10.1016/j.niox.2019.02.005
    19. Weizhun Yang, Sherif Ramadan, Jared Orwenyo, Tayeb Kakeshpour, Thomas Diaz, Yigitcan Eken, Miloslav Sanda, James E. Jackson, Angela K. Wilson, Xuefei Huang. Chemoenzymatic synthesis of glycopeptides bearing rare N-glycan sequences with or without bisecting GlcNAc. Chemical Science 2018, 9 (43) , 8194-8206. https://doi.org/10.1039/C8SC02457J
    20. Janick Raßloff, Qimeng Zhang, Petra Mischnick. Potential of dibutyltin oxide for the manno/gluco- and regioselective methylation of Konjac glucomannan. Cellulose 2018, 25 (9) , 4929-4940. https://doi.org/10.1007/s10570-018-1911-3
    21. Dong Wang, De-Cai Xiong, Xin-Shan Ye. A five-component one-pot synthesis of phosphatidylinositol pentamannoside (PIM5). Chinese Chemical Letters 2018, 29 (9) , 1340-1342. https://doi.org/10.1016/j.cclet.2017.12.014
    22. Pei‐Qiang Huang. Principles for Synthetic Efficiency and Expansion of the Field. 2018, 27-65. https://doi.org/10.1002/9781118940228.ch1
    23. M. Eugenia Giorgi, Rosana Lopez, Rosalia Agusti, Carla Marino, Rosa M. de Lederkremer. Synthesis of a model trisaccharide for studying the interplay between the anti α-Gal antibody and the trans-sialidase reactions in Trypanosoma cruzi. Carbohydrate Research 2017, 450 , 30-37. https://doi.org/10.1016/j.carres.2017.08.007
    24. Abhishek Santra, Yanhong Li, Hai Yu, Teri J. Slack, Peng George Wang, Xi Chen. Highly efficient chemoenzymatic synthesis and facile purification of α-Gal pentasaccharyl ceramide Galα3nLc 4 βCer. Chemical Communications 2017, 53 (59) , 8280-8283. https://doi.org/10.1039/C7CC04090C
    25. Marcelo Fiori Marchiori, Dênio Emanuel Pires Souto, Leandro Oliveira Bortot, João Francisco Pereira, Lauro Tatsuo Kubota, Richard D. Cummings, Marcelo Dias-Baruffi, Ivone Carvalho, Vanessa Leiria Campo. Synthetic 1,2,3-triazole-linked glycoconjugates bind with high affinity to human galectin-3. Bioorganic & Medicinal Chemistry 2015, 23 (13) , 3414-3425. https://doi.org/10.1016/j.bmc.2015.04.044
    26. Medel Manuel L. Zulueta, Donala Janreddy, Shang‐Cheng Hung. One‐Pot Methods for the Protection and Assembly of Sugars. Israel Journal of Chemistry 2015, 55 (3-4) , 347-359. https://doi.org/10.1002/ijch.201400171
    27. De-Cai Xiong, An-Qi Yang, Yang Yu, Xin-Shan Ye. 2-Pyridyl glycoside: an alternative glycosyl donor in preactivation protocol. Tetrahedron Letters 2015, 56 (1) , 211-214. https://doi.org/10.1016/j.tetlet.2014.11.066
    28. Nabamita Basu, Mana Mohan Mukherjee, Rina Ghosh. Synthetic routes toward the trisaccharide related to the lipopolysaccharide of Burkholderia sp. HKI-402 (B4). RSC Adv. 2014, 4 (96) , 54084-54090. https://doi.org/10.1039/C4RA03954H
    29. Peng Peng, Han Liu, Jianzhi Gong, John M. Nicholls, Xuechen Li. A facile synthesis of sialylated oligolactosamine glycans from lactose via the Lafont intermediate. Chem. Sci. 2014, 5 (9) , 3634-3639. https://doi.org/10.1039/C4SC01013B
    30. Sneha C. Ranade, Alexei V. Demchenko. Mechanism of Chemical Glycosylation: Focus on the Mode of Activation and Departure of Anomeric Leaving Groups. Journal of Carbohydrate Chemistry 2013, 32 (1) , 1-43. https://doi.org/10.1080/07328303.2012.749264
    31. Min Fang, Li Gu, Guofeng Gu, Junqiang Fang. Facile Synthesis and Antitumor Activities of Timosaponin AIII and Its Analogs. Journal of Carbohydrate Chemistry 2012, 31 (3) , 187-202. https://doi.org/10.1080/07328303.2011.639966
    32. Che‐Hsiung Hsu, Shang‐Cheng Hung, Chung‐Yi Wu, Chi‐Huey Wong. Auf dem Weg zur automatisierten Oligosaccharid‐ Synthese. Angewandte Chemie 2011, 123 (50) , 12076-12129. https://doi.org/10.1002/ange.201100125
    33. Che‐Hsiung Hsu, Shang‐Cheng Hung, Chung‐Yi Wu, Chi‐Huey Wong. Toward Automated Oligosaccharide Synthesis. Angewandte Chemie International Edition 2011, 50 (50) , 11872-11923. https://doi.org/10.1002/anie.201100125
    34. Takafumi Ohara, Alexander Adibekian, Davide Esposito, Pierre Stallforth, Peter H. Seeberger. Towards the synthesis of a Yersinia pestis cell wall polysaccharide: enantioselective synthesis of an l-glycero-d-manno-heptose building block. Chemical Communications 2010, 46 (23) , 4106. https://doi.org/10.1039/c000784f
    35. Guokai Lü, Peng Wang, Qingchao Liu, Zaihong Zhang, Wei Zhang, Yingxia Li. Reactivity‐based One‐pot Synthesis of Immunosuppressive Glycolipids from the Caribbean Sponge Plakortis simplex. Chinese Journal of Chemistry 2009, 27 (11) , 2217-2222. https://doi.org/10.1002/cjoc.200990372
    36. Thomas J. Boltje, Therese Buskas, Geert-Jan Boons. Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research. Nature Chemistry 2009, 1 (8) , 611-622. https://doi.org/10.1038/nchem.399
    37. David J. Harvey. Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2003–2004. Mass Spectrometry Reviews 2009, 28 (2) , 273-361. https://doi.org/10.1002/mas.20192
    38. Xiaoning Li, Lijun Huang, Xiche Hu, Xuefei Huang. Thio-arylglycosides with various aglyconpara-substituents: a probe for studying chemical glycosylation reactions. Org. Biomol. Chem. 2009, 7 (1) , 117-127. https://doi.org/10.1039/B813048E
    39. Sang-Hyun Son, Chiharu Tano, Tetsuya Furuike, Nobuo Sakairi. Synthesis of a tetrasaccharide repeating unit of O-antigenic polysaccharide of Salmonella enteritidis by use of unique and odorless dodecyl thioglycosyl donors. Tetrahedron Letters 2008, 49 (36) , 5289-5292. https://doi.org/10.1016/j.tetlet.2008.06.097
    40. Rodrigo B. Andrade. Glycan Synthesis: Key Strategies. 2008, 1-12. https://doi.org/10.1002/9780470048672.wecb194
    41. Wei Zhong, Geert‐Jan Boons, David Crich, Albert A. Bowers. Glycoside Synthesis from 1‐Sulfur/Selenium‐Substituted Derivatives: Sections 4.1 and 4.2. 2008, 261-329. https://doi.org/10.1002/9783527621644.ch4a
    42. Zhongwu Guo. Chemical Synthesis of Complex Carbohydrates. 2008, 59-83. https://doi.org/10.1016/B978-0-08-054816-6.00003-3
    43. Alexander Adibekian, Pascal Bindschädler, Mattie S. M. Timmer, Christian Noti, Nina Schützenmeister, Peter H. Seeberger. De Novo Synthesis of Uronic Acid Building Blocks for Assembly of Heparin Oligosaccharides. Chemistry – A European Journal 2007, 13 (16) , 4510-4522. https://doi.org/10.1002/chem.200700141
    44. Aileen F.G. Bongat, Alexei V. Demchenko. Recent trends in the synthesis of O-glycosides of 2-amino-2-deoxysugars. Carbohydrate Research 2007, 342 (3-4) , 374-406. https://doi.org/10.1016/j.carres.2006.10.021
    45. X. Huang, Z. Wang. Strategies in Oligosaccharide Synthesis. 2007, 379-413. https://doi.org/10.1016/B978-044451967-2/00011-8
    46. Yuhang Wang, Xin-Shan Ye, Li-He Zhang. Oligosaccharide assembly by one-pot multi-step strategy. Organic & Biomolecular Chemistry 2007, 5 (14) , 2189. https://doi.org/10.1039/b704586g
    47. Changning Wang, Qin Li, Haisheng Wang, Li-He Zhang, Xin-Shan Ye. A new one-pot synthesis of Gb3 and isoGb3 trisaccharide analogues. Tetrahedron 2006, 62 (50) , 11657-11662. https://doi.org/10.1016/j.tet.2006.09.058
    48. Akihiro Imamura, Akiyoshi Kimura, Hiromune Ando, Hideharu Ishida, Makoto Kiso. Extended Applications of Di‐ tert ‐butylsilylene‐Directed α‐Predominant Galactosylation Compatible with C2‐Participating Groups toward the Assembly of Various Glycosides. Chemistry – A European Journal 2006, 12 (34) , 8862-8870. https://doi.org/10.1002/chem.200600832
    49. Christian Noti, Jose L. de Paz, Laura Polito, Peter H. Seeberger. Preparation and Use of Microarrays Containing Synthetic Heparin Oligosaccharides for the Rapid Analysis of Heparin–Protein Interactions. Chemistry – A European Journal 2006, 12 (34) , 8664-8686. https://doi.org/10.1002/chem.200601103
    50. Lijun Huang, Zhen Wang, Xiaoning Li, Xin-shan Ye, Xuefei Huang. Iterative one-pot syntheses of chitotetroses. Carbohydrate Research 2006, 341 (10) , 1669-1679. https://doi.org/10.1016/j.carres.2006.01.007
    51. James T. Smoot, Papapida Pornsuriyasak, Alexei V. Demchenko. Development of an Arming Participating Group for Stereoselective Glycosylation and Chemoselective Oligosaccharide Synthesis. Angewandte Chemie 2005, 117 (43) , 7285-7288. https://doi.org/10.1002/ange.200502694
    52. James T. Smoot, Papapida Pornsuriyasak, Alexei V. Demchenko. Development of an Arming Participating Group for Stereoselective Glycosylation and Chemoselective Oligosaccharide Synthesis. Angewandte Chemie International Edition 2005, 44 (43) , 7123-7126. https://doi.org/10.1002/anie.200502694
    53. David Crich, Abhisek Banerjee, Wenju Li, Qingjia Yao. Improved Synthesis of 1‐Benzenesulfinyl Piperidine and Analogs for the Activation of Thioglycosides in Conjunction with Trifluoromethanesulfonic Anhydride*. Journal of Carbohydrate Chemistry 2005, 24 (4-6) , 415-424. https://doi.org/10.1081/CAR-200066978
    54. Yuhang Wang, Qingyan Yan, Jingping Wu, Li-He Zhang, Xin-Shan Ye. A new one-pot synthesis of α-Gal epitope derivatives involved in the hyperacute rejection response in xenotransplantation. Tetrahedron 2005, 61 (17) , 4313-4321. https://doi.org/10.1016/j.tet.2005.02.023
    55. Yuhang Wang, Xuefei Huang, Li-He Zhang, Xin-Shan Ye. A Four-Component One-Pot Synthesis of ?-Gal Pentasaccharide.. ChemInform 2005, 36 (11) https://doi.org/10.1002/chin.200511198
    56. Jeroen D. C. Codée, Remy E. J. N. Litjens, Leendert J. van den Bos, Herman S. Overkleeft, Gijsbert A. van der Marel. Thioglycosides in sequential glycosylation strategies. Chemical Society Reviews 2005, 34 (9) , 769. https://doi.org/10.1039/b417138c

    Organic Letters

    Cite this: Org. Lett. 2004, 6, 24, 4415–4417
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol0483246
    Published October 27, 2004
    Copyright © 2004 American Chemical Society

    Article Views

    1772

    Altmetric

    -

    Citations

    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.