Chemoenzymatic Approach for the Preparation of Asymmetric Bi-, Tri-, and Tetra-Antennary N-Glycans from a Common PrecursorClick to copy article linkArticle link copied!
- Ivan A. Gagarinov
- Tiehai Li
- Javier Sastre Toraño
- Tomislav Caval
- Apoorva D. Srivastava
- John A. W. Kruijtzer
- Albert J. R. Heck
- Geert-Jan Boons
Abstract

Progress in glycoscience is hampered by a lack of well-defined complex oligosaccharide standards that are needed to fabricate the next generation of microarrays, to develop analytical protocols to determine exact structures of isolated glycans, and to elucidate pathways of glycan biosynthesis. We describe here a chemoenzymatic methodology that makes it possible, for the first time, to prepare any bi-, tri-, and tetra-antennary asymmetric N-glycan from a single precursor. It is based on the chemical synthesis of a tetra-antennary glycan that has N-acetylglucosamine (GlcNAc), N-acetyllactosamine (LacNAc), and unnatural Galα(1,4)-GlcNAc and Manβ(1,4)-GlcNAc appendages. Mammalian glycosyltransferases recognize only the terminal LacNAc moiety as a substrate, and thus this structure can be uniquely extended. Next, the β-GlcNAc terminating antenna can be converted into LacNAc by galactosylation and can then be enzymatically modified into a complex structure. The unnatural α-Gal and β-Man terminating antennae can sequentially be decaged by an appropriate glycosidase to liberate a terminal β-GlcNAc moiety, which can be converted into LacNAc and then elaborated by a panel of glycosyltransferases. Asymmetric bi- and triantennary glycans could be obtained by removal of a terminal β-GlcNAc moiety by treatment with β-N-acetylglucosaminidase and selective extension of the other arms. The power of the methodology is demonstrated by the preparation of an asymmetric tetra-antennary N-glycan found in human breast carcinoma tissue, which represents the most complex N-glycan ever synthesized. Multistage mass spectrometry of the two isomeric triantennary glycans uncovered unique fragment ions that will facilitate identification of exact structures of glycans in biological samples.
Cited By
Smart citations by scite.ai include citation statements extracted from the full text of the citing article. The number of the statements may be higher than the number of citations provided by ACS Publications if one paper cites another multiple times or lower if scite has not yet processed some of the citing articles.
This article is cited by 74 publications.
- Dongfang Li, Can Li, Qiushi Chen, Haiyan Zhou, Zhixiang Zhong, Zirong Huang, Han Liu, Xuechen Li. Generalizing a Ligation Site at the N-Glycosylation Sequon for Chemical Synthesis of N-Linked Glycopeptides and Glycoproteins. Journal of the American Chemical Society 2024, 146
(42)
, 29017-29027. https://doi.org/10.1021/jacs.4c09996
- Yunfei Wu, Gerlof P. Bosman, Digantkumar Chapla, Chin Huang, Kelley W. Moremen, Robert P. de Vries, Geert-Jan Boons. A Biomimetic Synthetic Strategy Can Provide Keratan Sulfate I and II Oligosaccharides with Diverse Fucosylation and Sulfation Patterns. Journal of the American Chemical Society 2024, 146
(13)
, 9230-9240. https://doi.org/10.1021/jacs.4c00363
- Chang-Cheng Liu, Jinfeng Ye, Hongzhi Cao. Chemical Evolution of Enzyme-Catalyzed Glycosylation. Accounts of Chemical Research 2024, 57
(4)
, 636-647. https://doi.org/10.1021/acs.accounts.3c00754
- Joshua C.L. Maliepaard, J. Mirjam A. Damen, Geert-Jan P.H. Boons, Karli R. Reiding. Glycoproteomics-Compatible MS/MS-Based Quantification of Glycopeptide Isomers. Analytical Chemistry 2023, 95
(25)
, 9605-9614. https://doi.org/10.1021/acs.analchem.3c01319
- Jincai Wang, Yingle Feng, Taotao Sun, Qi Zhang, Yonghai Chai. Photolabile 2-(2-Nitrophenyl)-propyloxycarbonyl (NPPOC) for Stereoselective Glycosylation and Its Application in Consecutive Assembly of Oligosaccharides. The Journal of Organic Chemistry 2022, 87
(5)
, 3402-3421. https://doi.org/10.1021/acs.joc.1c03006
- Zhaoyu Hu, Mounir Benkoulouche, Louis-Antoine Barel, Guillaume Le Heiget, Akli Ben Imeddourene, Yann Le Guen, Nelly Monties, Catherine Guerreiro, Magali Remaud-Siméon, Claire Moulis, Isabelle André, Laurence A. Mulard. Convergent Chemoenzymatic Strategy to Deliver a Diversity of Shigella flexneri Serotype-Specific O-Antigen Segments from a Unique Lightly Protected Tetrasaccharide Core. The Journal of Organic Chemistry 2021, 86
(3)
, 2058-2075. https://doi.org/10.1021/acs.joc.0c00777
- Rajendra S. Rohokale, Qingjiang Li, Zhongwu Guo. A Diversity-Oriented Strategy for Chemical Synthesis of Glycosphingolipids: Synthesis of Glycosphingolipid LcGg4 and Its Analogues and Derivatives. The Journal of Organic Chemistry 2021, 86
(2)
, 1633-1648. https://doi.org/10.1021/acs.joc.0c02490
- Sujeet Pawar, Li Hsu, Thatikonda Narendar Reddy, Mettu Ravinder, Chien-Tai Ren, Yu-Wei Lin, Yang-Yu Cheng, Tzu-Wen Lin, Tsui-Ling Hsu, Sheng-Kai Wang, Chi-Huey Wong, Chung-Yi Wu. Synthesis of Asymmetric N-Glycans as Common Core Substrates for Structural Diversification through Selective Enzymatic Glycosylation. ACS Chemical Biology 2020, 15
(9)
, 2382-2394. https://doi.org/10.1021/acschembio.0c00359
- Kim Le Mai Hoang, Alonso Pardo-Vargas, Yuntao Zhu, Yang Yu, Mirco Loria, Martina Delbianco, Peter H. Seeberger. Traceless Photolabile Linker Expedites the Chemical Synthesis of Complex Oligosaccharides by Automated Glycan Assembly. Journal of the American Chemical Society 2019, 141
(22)
, 9079-9086. https://doi.org/10.1021/jacs.9b03769
- 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
- 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
- Liuqing Wen, Garrett Edmunds, Christopher Gibbons, Jiabin Zhang, Madhusudhan Reddy Gadi, Hailiang Zhu, Junqiang Fang, Xianwei Liu, Yun Kong, Peng George Wang. Toward Automated Enzymatic Synthesis of Oligosaccharides. Chemical Reviews 2018, 118
(17)
, 8151-8187. https://doi.org/10.1021/acs.chemrev.8b00066
- Chao Li, Lai-Xi Wang. Chemoenzymatic Methods for the Synthesis of Glycoproteins. Chemical Reviews 2018, 118
(17)
, 8359-8413. https://doi.org/10.1021/acs.chemrev.8b00238
- Yuta Maki, Takanori Mima, Ryo Okamoto, Masayuki Izumi, and Yasuhiro Kajihara . Semisynthesis of Complex-Type Biantennary Oligosaccharides Containing Lactosamine Repeating Units from a Biantennary Oligosaccharide Isolated from a Natural Source. The Journal of Organic Chemistry 2018, 83
(1)
, 443-451. https://doi.org/10.1021/acs.joc.7b02485
- Ivan A. Gagarinov, Lin Liu, Geert-Jan Boons. Chemical Synthesis of Oligosaccharides Derived from
Streptococcus pneumoniae
Serotype 35B and D to Investigate Binding of Complement and Serum Factors. 2025https://doi.org/10.1101/2025.01.28.635287
- Carmanah D. Hunter, Christopher W. Cairo. Detection Strategies for Sialic Acid and Sialoglycoconjugates. ChemBioChem 2024, 25
(23)
https://doi.org/10.1002/cbic.202400402
- Shengzhou Ma, Jinhua Gao, Yinping Tian, Liuqing Wen. Recent progress in chemoenzymatic synthesis of human glycans. Organic & Biomolecular Chemistry 2024, 22
(38)
, 7767-7785. https://doi.org/10.1039/D4OB01006J
- Fangyu Wei, Lanlan Zang, Pengfei Zhang, Jiabin Zhang, Liuqing Wen. Concise chemoenzymatic synthesis of N-glycans. Chem 2024, 10
(9)
, 2844-2860. https://doi.org/10.1016/j.chempr.2024.05.006
- Zhi-Fei Hu, Kan Zhong, Hongzhi Cao. Recent advances in enzymatic and chemoenzymatic synthesis of N- and O-glycans. Current Opinion in Chemical Biology 2024, 78 , 102417. https://doi.org/10.1016/j.cbpa.2023.102417
- Mehman Bunyatov, Margreet A. Wolfert, Lin Liu, Ruth Huizinga, Marco W. J. Schreurs, Bart C. Jacobs, Geert-Jan Boons. Chemoenzymatic synthesis of human natural killer-1-containing glycans and application as serum antibodies probes. Nature Synthesis 2024, 3
(1)
, 85-98. https://doi.org/10.1038/s44160-023-00394-4
- Joshua M Kofsky, Jonathan L Babulic, Marie E Boddington, Fabiola V De León González, Chantelle J Capicciotti. Glycosyltransferases as versatile tools to study the biology of glycans. Glycobiology 2023, 33
(11)
, 888-910. https://doi.org/10.1093/glycob/cwad092
- Koichi Fukase, Yoshiyuki Manabe, Atsushi Shimoyama. Diacetyl strategy for synthesis of NHAc containing glycans: enhancing glycosylation reactivity via diacetyl imide protection. Frontiers in Chemistry 2023, 11 https://doi.org/10.3389/fchem.2023.1319883
- Chih-Lan Lin, Mirat Sojitra, Eric J. Carpenter, Ellen S. Hayhoe, Susmita Sarkar, Elizabeth A. Volker, Chao Wang, Duong T. Bui, Loretta Yang, John S. Klassen, Peng Wu, Matthew S. Macauley, Todd L. Lowary, Ratmir Derda. Chemoenzymatic synthesis of genetically-encoded multivalent liquid N-glycan arrays. Nature Communications 2023, 14
(1)
https://doi.org/10.1038/s41467-023-40900-y
- Wenjing Ma, Zhuojia Xu, Yuhan Jiang, Jialin Liu, Dandan Xu, Wei Huang, Tiehai Li. Divergent Enzymatic Assembly of a Comprehensive 64‐Membered IgG
N
‐Glycan Library for Functional Glycomics. Advanced Science 2023, 10
(30)
https://doi.org/10.1002/advs.202303832
- David J. Harvey. Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2017–2018. Mass Spectrometry Reviews 2023, 42
(1)
, 227-431. https://doi.org/10.1002/mas.21721
- Yen-Pang Hsu, Deeptak Verma, Shuwen Sun, Caroline McGregor, Ian Mangion, Benjamin F. Mann. Successive remodeling of IgG glycans using a solid-phase enzymatic platform. Communications Biology 2022, 5
(1)
https://doi.org/10.1038/s42003-022-03257-4
- 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
- Mohammed Tarique Anwar, Avijit K. Adak, Sachin Kisan Kawade, Hsin-Ru Wu, Takashi Angata, Chun-Cheng Lin. Combining CuAAC reaction enables sialylated Bi- and triantennary pseudo mannose N-glycans for investigating Siglec-7 interactions. Bioorganic & Medicinal Chemistry 2022, 67 , 116839. https://doi.org/10.1016/j.bmc.2022.116839
- Javier Mauricio Melo Diaz, Alan B. Moran, Simon R. Peel, Jenifer L. Hendel, Daniel I. R. Spencer. Egg yolk sialylglycopeptide: purification, isolation and characterization of
N
-glycans from minor glycopeptide species. Organic & Biomolecular Chemistry 2022, 20
(24)
, 4905-4914. https://doi.org/10.1039/D2OB00615D
- Yuan Zheng, Jiabin Zhang, Jeffrey Meisner, Wanjin Li, Yawen Luo, Fangyu Wei, Liuqing Wen. Cofactor‐Driven Cascade Reactions Enable the Efficient Preparation of Sugar Nucleotides. Angewandte Chemie 2022, 134
(20)
https://doi.org/10.1002/ange.202115696
- Yuan Zheng, Jiabin Zhang, Jeffrey Meisner, Wanjin Li, Yawen Luo, Fangyu Wei, Liuqing Wen. Cofactor‐Driven Cascade Reactions Enable the Efficient Preparation of Sugar Nucleotides. Angewandte Chemie International Edition 2022, 61
(20)
https://doi.org/10.1002/anie.202115696
- Mohammed Tarique Anwar, Sachin Kisan Kawade, Yi-Ren Huo, Avijit K. Adak, Deepa Sridharan, Yan-Ting Kuo, Chen-Yo Fan, Hsin-Ru Wu, Yun-Sheng Lee, Takashi Angata, Chun-Cheng Lin. Sugar nucleotide regeneration system for the synthesis of Bi- and triantennary N-glycans and exploring their activities against siglecs. European Journal of Medicinal Chemistry 2022, 232 , 114146. https://doi.org/10.1016/j.ejmech.2022.114146
- Marco Brito-Arias. O-Glycoside Formation. 2022, 101-228. https://doi.org/10.1007/978-3-030-97854-9_2
- Asuka Shirakawa, Yoshiyuki Manabe, Roberta Marchetti, Kumpei Yano, Seiji Masui, Alba Silipo, Antonio Molinaro, Koichi Fukase. Chemical Synthesis of Sialyl
N
‐Glycans and Analysis of Their Recognition by Neuraminidase. Angewandte Chemie 2021, 133
(46)
, 24891-24898. https://doi.org/10.1002/ange.202111035
- Asuka Shirakawa, Yoshiyuki Manabe, Roberta Marchetti, Kumpei Yano, Seiji Masui, Alba Silipo, Antonio Molinaro, Koichi Fukase. Chemical Synthesis of Sialyl
N
‐Glycans and Analysis of Their Recognition by Neuraminidase. Angewandte Chemie International Edition 2021, 60
(46)
, 24686-24693. https://doi.org/10.1002/anie.202111035
- Mingli Liu, Xianjin Qin, Xin‐Shan Ye. Glycan Assembly Strategy: From Concept to Application. The Chemical Record 2021, 21
(11)
, 3256-3277. https://doi.org/10.1002/tcr.202100183
- Apoorva D. Srivastava, Luca Unione, Mehman Bunyatov, Ivan A. Gagarinov, Sandra Delgado, Nicola G. A. Abrescia, Ana Ardá, Geert‐Jan Boons. Chemoenzymatic Synthesis of Complex
N
‐Glycans of the Parasite
S. mansoni
to Examine the Importance of Epitope Presentation on DC‐SIGN recognition. Angewandte Chemie 2021, 133
(35)
, 19436-19445. https://doi.org/10.1002/ange.202105647
- Apoorva D. Srivastava, Luca Unione, Mehman Bunyatov, Ivan A. Gagarinov, Sandra Delgado, Nicola G. A. Abrescia, Ana Ardá, Geert‐Jan Boons. Chemoenzymatic Synthesis of Complex
N
‐Glycans of the Parasite
S. mansoni
to Examine the Importance of Epitope Presentation on DC‐SIGN recognition. Angewandte Chemie International Edition 2021, 60
(35)
, 19287-19296. https://doi.org/10.1002/anie.202105647
- Irina Dyukova, Ahmed Ben Faleh, Stephan Warnke, Natalia Yalovenko, Vasyl Yatsyna, Priyanka Bansal, Thomas R. Rizzo. A new approach for identifying positional isomers of glycans cleaved from monoclonal antibodies. The Analyst 2021, 146
(15)
, 4789-4795. https://doi.org/10.1039/D1AN00780G
- Yoshiyuki Manabe. Chemical Biology Study on N-glycans. Trends in Glycoscience and Glycotechnology 2021, 33
(193)
, E63-E67. https://doi.org/10.4052/tigg.2109.2E
- Yoshiyuki Manabe. Chemical Biology Study on N-glycans. Trends in Glycoscience and Glycotechnology 2021, 33
(193)
, J63-J68. https://doi.org/10.4052/tigg.2109.2J
- Hsin-Kai Tseng, Yung-Yu Su, Ting-Wei Chang, Hsin-Chien Liu, Pei-Jhen Li, Pei-Yun Chiang, Chun-Cheng Lin. Acceptor-mediated regioselective enzyme catalyzed sialylation: chemoenzymatic synthesis of GAA-7 ganglioside glycan. Chemical Communications 2021, 57
(28)
, 3468-3471. https://doi.org/10.1039/D1CC00653C
- Liting Zhao, Zhongbao Ma, Jian Yin, Guiyang Shi, Zhongyang Ding. Biological strategies for oligo/polysaccharide synthesis: biocatalyst and microbial cell factory. Carbohydrate Polymers 2021, 258 , 117695. https://doi.org/10.1016/j.carbpol.2021.117695
- Asuka Shirakawa, Yoshiyuki Manabe, Koichi Fukase. Recent Advances in the Chemical Biology of N-Glycans. Molecules 2021, 26
(4)
, 1040. https://doi.org/10.3390/molecules26041040
- Masanori Yamaguchi, Kenji Yamamoto. Chemo-Enzymatic Syntheses of Oligosaccharides and Glycoconjugates. 2021, 525-547. https://doi.org/10.1016/B978-0-12-819475-1.00011-0
- N. de Haan, M. Wuhrer, L.R. Ruhaak. Mass spectrometry in clinical glycomics: The path from biomarker identification to clinical implementation. Clinical Mass Spectrometry 2020, 18 , 1-12. https://doi.org/10.1016/j.clinms.2020.08.001
- Ying Zhang, Yuyang Zhu, Yi Lasanajak, David F. Smith, Xuezheng Song. O-Benzylhydroxylamine (BHA) as a Cleavable Tag for Isolation and Purification of Reducing Glycans. SLAS Technology 2020, 25
(4)
, 388-396. https://doi.org/10.1177/2472630319898150
- Qiang Chao, Yi Ding, Zheng-Hui Chen, Meng-Hai Xiang, Ning Wang, Xiao-Dong Gao. Recent Progress in Chemo-Enzymatic Methods for the Synthesis of N-Glycans. Frontiers in Chemistry 2020, 8 https://doi.org/10.3389/fchem.2020.00513
- Hanne L. P. Tytgat, Chia-wei Lin, Mikail D. Levasseur, Markus B. Tomek, Christoph Rutschmann, Jacqueline Mock, Nora Liebscher, Naohiro Terasaka, Yusuke Azuma, Michael Wetter, Martin F. Bachmann, Donald Hilvert, Markus Aebi, Timothy G. Keys. Cytoplasmic glycoengineering enables biosynthesis of nanoscale glycoprotein assemblies. Nature Communications 2019, 10
(1)
https://doi.org/10.1038/s41467-019-13283-2
- Luuk Mestrom, Marta Przypis, Daria Kowalczykiewicz, André Pollender, Antje Kumpf, Stefan R. Marsden, Isabel Bento, Andrzej B. Jarzębski, Katarzyna Szymańska, Arkadiusz Chruściel, Dirk Tischler, Rob Schoevaart, Ulf Hanefeld, Peter-Leon Hagedoorn. Leloir Glycosyltransferases in Applied Biocatalysis: A Multidisciplinary Approach. International Journal of Molecular Sciences 2019, 20
(21)
, 5263. https://doi.org/10.3390/ijms20215263
- Julia Weber, Dennis Svatunek, Simon Krauter, Gregor Tegl, Christian Hametner, Paul Kosma, Hannes Mikula. 2-
O
-Benzyloxycarbonyl protected glycosyl donors: a revival of carbonate-mediated anchimeric assistance for diastereoselective glycosylation. Chemical Communications 2019, 55
(83)
, 12543-12546. https://doi.org/10.1039/C9CC07194F
- Alyssa M. McQuillan, Lauren Byrd-Leotis, Jamie Heimburg-Molinaro, Richard D. Cummings. Natural and Synthetic Sialylated Glycan Microarrays and Their Applications. Frontiers in Molecular Biosciences 2019, 6 https://doi.org/10.3389/fmolb.2019.00088
- Qiongyu Li, Yixuan Xie, Maurice Wong, Carlito Lebrilla. Characterization of Cell Glycocalyx with Mass Spectrometry Methods. Cells 2019, 8
(8)
, 882. https://doi.org/10.3390/cells8080882
- Wanyi Guan, Garrett A. Edmunds, Zhigang Wu, Lei Li. Synthetically Useful Glycosyltransferases for the Access of Mammalian Glycomes. 2019, 46-82. https://doi.org/10.1039/9781788016575-00046
- Yu-Hsuan Lih, Sachin S. Shivatare, Chung-Yi Wu. Chemical Synthesis of
N
-Glycans. 2019, 83-104. https://doi.org/10.1039/9781788016575-00083
- Lei Li, Wanyi Guan, Zhigang Wu, Peng G. Wang. Chemoenzymatic Synthesis of
N
-Glycans. 2019, 105-124. https://doi.org/10.1039/9781788016575-00105
- Hai Yu, Xi Chen. Enzymatic and Chemoenzymatic Synthesis of Human Milk Oligosaccharides (HMOS). 2019, 254-280. https://doi.org/10.1039/9781788016575-00254
- Lei Li, Wanyi Guan, Zhigang Wu, Shuaishuai Wang. Current Stage of Commercial Glycan Microarrays. 2019, 447-460. https://doi.org/10.1039/9781788016575-00447
- Lin Liu, Anthony R. Prudden, Chantelle J. Capicciotti, Gerlof P. Bosman, Jeong-Yeh Yang, Digantkumar G. Chapla, Kelley W. Moremen, Geert-Jan Boons. Streamlining the chemoenzymatic synthesis of complex N-glycans by a stop and go strategy. Nature Chemistry 2019, 11
(2)
, 161-169. https://doi.org/10.1038/s41557-018-0188-3
- Wanqing Li, John B. McArthur, Xi Chen. Strategies for chemoenzymatic synthesis of carbohydrates. Carbohydrate Research 2019, 472 , 86-97. https://doi.org/10.1016/j.carres.2018.11.014
- Olga O. Zaytseva, Bas C. Jansen, Maja Hanić, Mia Mrčela, Genadij Razdorov, Ranko Stojković, Julija Erhardt, Ilija Brizić, Stipan Jonjić, Marija Pezer, Gordan Lauc. MIgGGly (mouse IgG glycosylation analysis) - a high-throughput method for studying Fc-linked IgG N-glycosylation in mice with nanoUPLC-ESI-MS. Scientific Reports 2018, 8
(1)
https://doi.org/10.1038/s41598-018-31844-1
- 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
- Karli R. Reiding, Albert Bondt, Vojtech Franc, Albert J.R. Heck. The benefits of hybrid fragmentation methods for glycoproteomics. TrAC Trends in Analytical Chemistry 2018, 108 , 260-268. https://doi.org/10.1016/j.trac.2018.09.007
- Unverzagt Carlo, Kajihara Yasuhiro. Recent advances in the chemical synthesis of N-linked glycoproteins. Current Opinion in Chemical Biology 2018, 46 , 130-137. https://doi.org/10.1016/j.cbpa.2018.07.004
- Supriya Dey, Sumit O. Bajaj, Tsung-I. Tsai, Hong-Jay Lo, Kevin Wu, Chi-Huey Wong. Synthesis of modular building blocks using glycosyl phosphate donors for the construction of asymmetric N-glycans. Tetrahedron 2018, 74
(41)
, 6003-6011. https://doi.org/10.1016/j.tet.2018.08.039
- Mirella Wawryszyn, Paul F. Sauter, Martin Nieger, Martin R. M. Koos, Christine Koehler, Burkhard Luy, Edward A. Lemke, Stefan Bräse. Synthesis of Azido‐Glycans for Chemical Glycomodification of Proteins. European Journal of Organic Chemistry 2018, 2018
(31)
, 4296-4305. https://doi.org/10.1002/ejoc.201800602
- Yoshiyuki Manabe, Hiroki Shomura, Naoya Minamoto, Masahiro Nagasaki, Yohei Takakura, Katsunori Tanaka, Alba Silipo, Antonio Molinaro, Koichi Fukase. Convergent Synthesis of a Bisecting
N
‐Acetylglucosamine (GlcNAc)‐Containing N‐Glycan. Chemistry – An Asian Journal 2018, 13
(12)
, 1544-1551. https://doi.org/10.1002/asia.201800367
- O. Aizpurua-Olaizola, J. Sastre Toraño, J.M. Falcon-Perez, C. Williams, N. Reichardt, G.-J. Boons. Mass spectrometry for glycan biomarker discovery. TrAC Trends in Analytical Chemistry 2018, 100 , 7-14. https://doi.org/10.1016/j.trac.2017.12.015
- Ning Wang, Sheng-Tao Li, Tian-Tian Lu, Hideki Nakanishi, Xiao-Dong Gao. Approaches towards the core pentasaccharide in N- linked glycans. Chinese Chemical Letters 2018, 29
(1)
, 35-39. https://doi.org/10.1016/j.cclet.2017.09.044
- Yuta Maki. Semisynthesis of Complex-type Triantennary Oligosaccharides from a Biantennary Oligosaccharide Isolated from Hen Egg Yolk. Trends in Glycoscience and Glycotechnology 2018, 30
(171)
, E15-E20. https://doi.org/10.4052/tigg.1707.4E
- Yuta Maki. Semisynthesis of Complex-type Triantennary Oligosaccharides from a Biantennary Oligosaccharide Isolated from Hen Egg Yolk. Trends in Glycoscience and Glycotechnology 2018, 30
(171)
, J1-J6. https://doi.org/10.4052/tigg.1707.4J
- Cheng‐Yueh Ting, Yu‐Wei Lin, Chung‐Yi Wu, Chi‐Huey Wong. Design of Disaccharide Modules for a Programmable One‐Pot Synthesis of Building Blocks with LacNAc Repeating Units for Asymmetric N‐Glycans. Asian Journal of Organic Chemistry 2017, 6
(12)
, 1800-1807. https://doi.org/10.1002/ajoc.201700393
- Maciej A. Walczak, Feng Zhu. Size Matters: Chemical Synthesis of a Homogenous Arabinogalactan 92‐mer. ChemBioChem 2017, 18
(18)
, 1789-1791. https://doi.org/10.1002/cbic.201700311
- Angie D. Calderon, Jun Zhou, Wanyi Guan, Zhigang Wu, Yuxi Guo, Jing Bai, Qing Li, Peng George Wang, Junqiang Fang, Lei Li. An enzymatic strategy to asymmetrically branched N-glycans. Organic & Biomolecular Chemistry 2017, 15
(35)
, 7258-7262. https://doi.org/10.1039/C7OB01765K
- Zhigang Wu, Yunpeng Liu, Lei Li, Xiu-Feng Wan, He Zhu, Yuxi Guo, Mohui Wei, Wanyi Guan, Peng George Wang. Decoding glycan protein interactions by a new class of asymmetric N-glycans. Organic & Biomolecular Chemistry 2017, 15
(42)
, 8946-8951. https://doi.org/10.1039/C7OB02303K
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.