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Journal articles on the topic 'Chemoselective glycosylation'

Author: Grafiati

Published: 9 March 2023

Last updated: 10 March 2023

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1

Nguyen, Hien M., Jennifer L. Poole, and David Y. Gin. "Chemoselective Iterative Dehydrative Glycosylation." Angewandte Chemie 113, no. 2 (January 19, 2001): 428–31. http://dx.doi.org/10.1002/1521-3757(20010119)113:2<428::aid-ange428>3.0.co;2-b.

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2

Nguyen, Hien M., Jennifer L. Poole, and David Y. Gin. "Chemoselective Iterative Dehydrative Glycosylation." Angewandte Chemie International Edition 40, no. 2 (January 19, 2001): 414–17. http://dx.doi.org/10.1002/1521-3773(20010119)40:2<414::aid-anie414>3.0.co;2-6.

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3

Yang, Weizhun, Bo Yang, Sherif Ramadan, and Xuefei Huang. "Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly." Beilstein Journal of Organic Chemistry 13 (October 9, 2017): 2094–114. http://dx.doi.org/10.3762/bjoc.13.207.

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Most glycosylation reactions are performed by mixing the glycosyl donor and acceptor together followed by the addition of a promoter. While many oligosaccharides have been synthesized successfully using this premixed strategy, extensive protective group manipulation and aglycon adjustment often need to be performed on oligosaccharide intermediates, which lower the overall synthetic efficiency. Preactivation-based glycosylation refers to strategies where the glycosyl donor is activated by a promoter in the absence of an acceptor. The subsequent acceptor addition then leads to the formation of the glycoside product. As donor activation and glycosylation are carried out in two distinct steps, unique chemoselectivities can be obtained. Successful glycosylation can be performed independent of anomeric reactivities of the building blocks. In addition, one-pot protocols have been developed that have enabled multiple-step glycosylations in the same reaction flask without the need for intermediate purification. Complex glycans containing both 1,2-cis and 1,2-trans linkages, branched oligosaccharides, uronic acids, sialic acids, modifications such as sulfate esters and deoxy glycosides have been successfully synthesized. The preactivation-based chemoselective glycosylation is a powerful strategy for oligosaccharide assembly complementing the more traditional premixed method.

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4

Figuereido, Ines, Alice Paiotta, Roberta Dal Magro, Francesca Tinelli, Roberta Corti, Francesca Re, Valeria Cassina, Enrico Caneva, Francesco Nicotra, and Laura Russo. "A New Approach for Glyco-Functionalization of Collagen-Based Biomaterials." International Journal of Molecular Sciences 20, no. 7 (April 9, 2019): 1747. http://dx.doi.org/10.3390/ijms20071747.

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The cell microenvironment plays a pivotal role in mediating cell adhesion, survival, and proliferation in physiological and pathological states. The relevance of extracellular matrix (ECM) proteins in cell fate control is an important issue to take into consideration for both tissue engineering and cell biology studies. The glycosylation of ECM proteins remains, however, largely unexplored. In order to investigate the physio-pathological effects of differential ECM glycosylation, the design of affordable chemoselective methods for ECM components glycosylation is desirable. We will describe a new chemoselective glycosylation approach exploitable in aqueous media and on non-protected substrates, allowing rapid access to glyco-functionalized biomaterials.

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5

Xiao, Ke, Yongxin Hu, Yongyong Wan, XinXin Li, Qin Nie, Hao Yan, Liming Wang, et al. "Hydrogen bond activated glycosylation under mild conditions." Chemical Science 13, no. 6 (2022): 1600–1607. http://dx.doi.org/10.1039/d1sc05772c.

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A mild glycosylation system was developed using glycosyl imidate donors and a charge-enhanced thiourea H-bond donor catalyst. The method can be used for the effective synthesis of O-, C-, S- and N-glycosides and chemoselective one-pot glycosylation.

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6

Nguyen, Hien M., Jennifer L. Poole, and David Y. Gin. "ChemInform Abstract: Chemoselective Iterative Dehydrative Glycosylation." ChemInform 32, no. 21 (May 26, 2010): no. http://dx.doi.org/10.1002/chin.200121063.

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7

Calce, Enrica, Giuseppe Digilio, Valeria Menchise, Michele Saviano, and Stefania De Luca. "Chemoselective Glycosylation of Peptides through S-Alkylation Reaction." Chemistry - A European Journal 24, no. 23 (April 14, 2018): 6231–38. http://dx.doi.org/10.1002/chem.201800265.

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8

Langenhan, Joseph M., Edouard Mullarky, Derek K. Rogalsky, James R. Rohlfing, Anja E. Tjaden, Halina M. Werner, Leonardo M. Rozal, and Steven A. Loskot. "Amphimedosides A–C: Synthesis, Chemoselective Glycosylation, And Biological Evaluation." Journal of Organic Chemistry 78, no. 4 (February 7, 2013): 1670–76. http://dx.doi.org/10.1021/jo302640y.

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9

Yang, You, Yao Li, and Biao Yu. "Chemoselective glycosylation of carboxylic acid with glycosyl ortho-hexynylbenzoates as donors." Tetrahedron Letters 51, no. 11 (March 2010): 1504–7. http://dx.doi.org/10.1016/j.tetlet.2010.01.039.

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10

Chiba, Hiroyuki, Setsuo Funasaka, Koichi Kiyota, and Teruaki Mukaiyama. "Catalytic and Chemoselective Glycosylation between “Armed” and “Disarmed” Glycosylp-Trifluoromethylbenzylthio-p-trifluoromethylphenyl Formimidates." Chemistry Letters 31, no. 7 (July 2002): 746–47. http://dx.doi.org/10.1246/cl.2002.746.

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11

Smoot, James T., Papapida Pornsuriyasak, and Alexei V. Demchenko. "Development of an Arming Participating Group for Stereoselective Glycosylation and Chemoselective Oligosaccharide Synthesis." Angewandte Chemie 117, no. 43 (November 4, 2005): 7285–88. http://dx.doi.org/10.1002/ange.200502694.

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12

Smoot, James T., Papapida Pornsuriyasak, and Alexei V. Demchenko. "Development of an Arming Participating Group for Stereoselective Glycosylation and Chemoselective Oligosaccharide Synthesis." Angewandte Chemie International Edition 44, no. 43 (November 4, 2005): 7123–26. http://dx.doi.org/10.1002/anie.200502694.

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13

Peri, Francesco. "ChemInform Abstract: Chemoselective Glycosylation Techniques for the Synthesis of Bioactive Neoglycoconjugates, Glyconanoparticles and Glycoarrays." ChemInform 44, no. 31 (July 11, 2013): no. http://dx.doi.org/10.1002/chin.201331233.

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14

Choudhury, Ambar Kumar, Indrani Mukherjee, Balaram Mukhopadhyay, and Nirmolendu Roy. "Communication: Chemoselective Glycosylation Based on Difference in the Reactivities of Ethyl and p-Tolyl Thioglycosides." Journal of Carbohydrate Chemistry 18, no. 3 (January 1, 1999): 361–67. http://dx.doi.org/10.1080/07328309908544001.

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15

Geurtsen, Richard, François Côté,, Michael G. Hahn, and Geert-Jan Boons. "Chemoselective Glycosylation Strategy for the Convergent Assembly of Phytoalexin-Elicitor Active Oligosaccharides and Their Photoreactive Derivatives." Journal of Organic Chemistry 64, no. 21 (October 1999): 7828–35. http://dx.doi.org/10.1021/jo990836o.

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16

Ni, Jiahong, Suddham Singh, and Lai-Xi Wang. "Synthesis of Maleimide-Activated Carbohydrates as Chemoselective Tags for Site-Specific Glycosylation of Peptides and Proteins." Bioconjugate Chemistry 14, no. 1 (January 2003): 232–38. http://dx.doi.org/10.1021/bc025617f.

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17

Tsai, Yow-Fu, Cheng-Hua Shih, Yu-Ting Su, Chun-Hsu Yao, Jang-Feng Lian, Chun-Chen Liao, Ching-Wu Hsia, Hao-Ai Shui, and Rashmi Rani. "The total synthesis of a ganglioside Hp-s1 analogue possessing neuritogenic activity by chemoselective activation glycosylation." Org. Biomol. Chem. 10, no. 5 (2012): 931–34. http://dx.doi.org/10.1039/c2ob06827c.

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18

Chiba, Hiroyuki, Setsuo Funasaka, Koichi Kiyota, and Teruaki Mukaiyama. "ChemInform Abstract: Catalytic and Chemoselective Glycosylation Between “Armed” and “Disarmed” Glycosyl p-Trifluoromethylbenzylthio-p-trifluoromethylphenyl Formimidates." ChemInform 33, no. 48 (May 18, 2010): no. http://dx.doi.org/10.1002/chin.200248200.

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19

Choudhury, Ambar Kumar, Indrani Mukherjee, Balaram Mukhopadhyay, and Nirmolendu Roy. "ChemInform Abstract: Chemoselective Glycosylation Based on Difference in the Reactivities of Ethyl and p-Tolyl Thioglycosides." ChemInform 30, no. 36 (June 13, 2010): no. http://dx.doi.org/10.1002/chin.199936237.

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20

Verma, Nitish, Zhijay Tu, Ming-Shiuan Lu, Shih-Hao Liu, Septila Renata, Riping Phang, Peng-Kai Liu, Bhaswati Ghosh, and Chun-Hung Lin. "Threshold of Thioglycoside Reactivity Difference Is Critical for Efficient Synthesis of Type I Oligosaccharides by Chemoselective Glycosylation." Journal of Organic Chemistry 86, no. 1 (December 15, 2020): 892–916. http://dx.doi.org/10.1021/acs.joc.0c02422.

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21

Dutta, Samrat, Swarbhanu Sarkar, Shyam Ji Gupta, and Asish Kumar Sen. "Use of iodine for efficient and chemoselective glycosylation with glycosyl ortho-alkynylbenzoates as donor in presence of thioglycosides." Tetrahedron Letters 54, no. 8 (February 2013): 865–70. http://dx.doi.org/10.1016/j.tetlet.2012.11.101.

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22

Zeng, Chen, Bin Sun, Xuefeng Cao, Hailiang Zhu, Olawale Micheal Oluwadahunsi, Ding Liu, He Zhu, et al. "Chemical Synthesis of Homogeneous Human E-Cadherin N-Linked Glycopeptides: Stereoselective Convergent Glycosylation and Chemoselective Solid-Phase Aspartylation." Organic Letters 22, no. 21 (October 12, 2020): 8349–53. http://dx.doi.org/10.1021/acs.orglett.0c02971.

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23

Geurtsen, Richard, Francois Cote, Michael G. Hahn, and Geert-Jan Boons. "ChemInform Abstract: Chemoselective Glycosylation Strategy for the Convergent Assembly of Phytoalexin-Elicitor Active Oligosaccharides and Their Photoreactive Derivatives." ChemInform 31, no. 5 (June 11, 2010): no. http://dx.doi.org/10.1002/chin.200005237.

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24

Jeanneret, Robin A., Charlotte E. Dalton, and John M. Gardiner. "Synthesis of Heparan Sulfate- and Dermatan Sulfate-Related Oligosaccharides via Iterative Chemoselective Glycosylation Exploiting Conformationally Disarmed [2.2.2] l-Iduronic Lactone Thioglycosides." Journal of Organic Chemistry 84, no. 23 (November 2019): 15063–78. http://dx.doi.org/10.1021/acs.joc.9b01594.

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25

Simeonova, Gergana, and Boyan Todorov. "MODIFICATION OF [18F]FDG BY THE FORMATION OF A HYDRAZONE BOND." Journal of IMAB - Annual Proceeding (Scientific Papers) 29, no. 1 (January 27, 2023): 4784–88. http://dx.doi.org/10.5272/jimab.2023291.4784.

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Purpose: The [18F]-fluorodeoxyglucose ([18F]-FDG) is known to be one of the most used radio-pharmaceuticals for positron emission tomography. [18F]-FDG allows the assessment of glycolytic activity, which is more enhanced in tumor cells than in normal cells. It is also used in the assessment of heart and neurological diseases. The aim of our work is to follow the possibility of modifying [18F]-fluorodeoxyglucose and to develop an indirect radiofluorination procedure applicable under standard clinical conditions. Material/Methods: In the clinic of nuclear medicine at the University Hospital Sta. Marina-Varna, for routine clinical purposes, [18F]-FDG is produced by the nucleophilic method of fluorination, using mannose triflate as a precursor. In addition to being used as a universal radiopharmaceutical, [18F]-FDG may be involved as a prosthetic group in biorthogonal reactions. [18F]-glycosylation by oxime or hydrazone formation is a chemoselective method for indirect radiofluorination of sensitive molecules. The process can improve the pharmacokinetics and stability of the labeled compounds in the blood. Results: We developed a method for modifying fluorine-deoxyglucose by forming a hydrazone bond with bifunctional tetrazine {3-[4-(6-phenyl-[1,2,4,5]-tetrazine-3-yl)-phenoxy]-propyl}-hydrazine) (Tz). The progress of the process and the product obtained were monitored by radio TLC. The radiolabeled tetrazine product will be used for future biorthogonal click reactions with trans-cyclooctene under physiological conditions.

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26

Ohira, Shuichi, Yoshiki Yamaguchi, Takashi Takahashi, and Hiroshi Tanaka. "The chemoselective O-glycosylation of alcohols in the presence of a phosphate diester and its application to the synthesis of oligomannosylated phosphatidyl inositols." Tetrahedron 71, no. 37 (September 2015): 6602–11. http://dx.doi.org/10.1016/j.tet.2015.06.041.

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27

Nakahara, Taku, Diane McCarthy, Yoshiaki Miura, and Hidehisa Asada. "High-throughput glycomics for discovery of cancer biomarkers." Journal of Clinical Oncology 30, no. 30_suppl (October 20, 2012): 9. http://dx.doi.org/10.1200/jco.2012.30.30_suppl.9.

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9 Background: While the importance of glycosylation in many cancers is well established, the use of glycomics in biomarker research has lagged behind genomics and proteomics. This is due, in part, to the lack of practical platforms capable of analyzing clinically relevant sample numbers. To address these challenges, we have developed a novel glycomics technology (the GlycanMap platform) that combines a high-throughput assay with custom bioinformatics and rapidly provides both biomarker candidates and information on the underlying biology. Methods: N-glycans were enzymatically released from their parent glycoproteins and captured on chemoselective beads. After washing to remove non-glycan components, purified glycans were derivatized to stabilize labile sialic acids and released from the beads. The steps described above were automated on a 96-well format robotics system to maximize throughput and reduce variability and can be performed in less than 24 hours. Released glycans were analyzed by MALDI-TOF MS using internal standards to facilitate quantitation. In addition to comparing individual glycans between groups, glycan changes were also analyzed with respect to known glycan biosynthetic pathways. Results: The automated assay was compatible with multiple biological sample types, including serum/plasma, tissue, and cell lysates. Human serum was used to assess assay performance and yielded 50-60 glycans with CVs of 10-15% and good linearity. The lower limit of detection was approximately 100 nM. The assay was applied to drug-treated colon cancer cells (HCT116) and revealed significant (> 2-fold) changes in 17 glycans. Projection of these glycan changes on the known N-glycan pathway showed that the most significant changes occurred in the medial-Golgi. Conclusions: We have developed and optimized a high-throughput glycomics platform to facilitate large-scale biomarker studies and assured its practical performance in terms of sensitivity, repeatability, and linearity. Application of this assay to drug-treated colon cancer cells demonstrated that projection of individual glycan changes against known glycan pathways provided additional information about biological mechanism and relevance.

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28

Geurtsen, Richard, Duncan S. Holmes, and Geert-Jan Boons. "Chemoselective Glycosylations. 2. Differences in Size of Anomeric Leaving Groups Can Be Exploited in Chemoselective Glycosylations." Journal of Organic Chemistry 62, no. 23 (November 1997): 8145–54. http://dx.doi.org/10.1021/jo971233k.

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29

Boons, Geert-Jan, Richard Geurtsen, and Duncan Holmes. "Chemoselective glycosylations (part 1): Differences in size of anomeric leaving groups can be exploited in chemoselective glycosylations." Tetrahedron Letters 36, no. 35 (August 1995): 6325–28. http://dx.doi.org/10.1016/0040-4039(95)01222-4.

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30

Geurtsen, Richard, and Geert-Jan Boons. "Chemoselective glycosylations of sterically hindered glycosyl acceptors." Tetrahedron Letters 43, no. 51 (December 2002): 9429–31. http://dx.doi.org/10.1016/s0040-4039(02)02334-1.

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31

Codée, Jeroen D. C., Leendert J. van den Bos, Remy E. J. N. Litjens, Herman S. Overkleeft, Constant A. A. van Boeckel, Jacques H. van Boom, and Gijs A. van der Marel. "Chemoselective glycosylations using sulfonium triflate activator systems." Tetrahedron 60, no. 5 (January 2004): 1057–64. http://dx.doi.org/10.1016/j.tet.2003.11.084.

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32

GEURTSEN, R., D. S. HOLMES, and G. J. BOONS. "ChemInform Abstract: Chemoselective Glycosylations. Part 2. Differences in Size of Anomeric Leaving Groups Can Be Exploited in Chemoselective Glycosylations." ChemInform 29, no. 15 (June 23, 2010): no. http://dx.doi.org/10.1002/chin.199815218.

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33

BOONS, G. J., R. GEURTSEN, and D. HOLMES. "ChemInform Abstract: Chemoselective Glycosylations. Part 1. Differences in Size of Anomeric Leaving Groups can be Exploited in Chemoselective Glycosylations." ChemInform 26, no. 50 (August 16, 2010): no. http://dx.doi.org/10.1002/chin.199550196.

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34

Kusumi, Shunichi, Kaname Sasaki, Sainan Wang, Tatsuya Watanabe, Daisuke Takahashi, and Kazunobu Toshima. "Effective and chemoselective glycosylations using 2,3-unsaturated sugars." Organic & Biomolecular Chemistry 8, no. 14 (2010): 3164. http://dx.doi.org/10.1039/c004204h.

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35

Kusumi, Shunichi, Sainan Wang, Tatsuya Watanabe, Kaname Sasaki, Daisuke Takahashi, and Kazunobu Toshima. "Chemoselective glycosylations using 2,3-unsaturated-4-keto glycosyl donors." Organic & Biomolecular Chemistry 8, no. 5 (2010): 988. http://dx.doi.org/10.1039/b925587g.

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36

Zhu, Tong, and Geert-Jan Boons. "Thioglycosides Protected as Trans-2,3-Cyclic Carbonates in Chemoselective Glycosylations." Organic Letters 3, no. 26 (December 2001): 4201–3. http://dx.doi.org/10.1021/ol016869j.

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37

Boons, Geert-Jan, and Tong Zhu. "Novel Regioselective Glycosylations for the Convergent and Chemoselective Assembly of Oligosaccharides." Synlett 1997, no. 7 (July 1997): 809–11. http://dx.doi.org/10.1055/s-1997-5767.

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38

Codée, Jeroen D. C., Remy E. J. N. Litjens, René den Heeten, Herman S. Overkleeft, Jacques H. van Boom, and Gijs A. van der Marel. "Ph2SO/Tf2O: a Powerful Promotor System in Chemoselective Glycosylations Using Thioglycosides." Organic Letters 5, no. 9 (May 2003): 1519–22. http://dx.doi.org/10.1021/ol034312t.

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39

Zhu, Tong, and Geert-Jan Boons. "ChemInform Abstract: Thioglycosides Protected as trans-2,3-Cyclic Carbonates in Chemoselective Glycosylations." ChemInform 33, no. 22 (May 21, 2010): no. http://dx.doi.org/10.1002/chin.200222190.

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40

BOONS, G. J., and T. ZHU. "ChemInform Abstract: Novel Regioselective Glycosylations for the Convergent and Chemoselective Assembly of Oligosaccharides." ChemInform 28, no. 46 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199746221.

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41

Miermont, Adeline, Youlin Zeng, Yuqing Jing, Xin-shan Ye, and Xuefei Huang. "Syntheses of LewisXand Dimeric LewisX: Construction of Branched Oligosaccharides by a Combination of Preactivation and Reactivity Based Chemoselective One-Pot Glycosylations." Journal of Organic Chemistry 72, no. 23 (November 2007): 8958–61. http://dx.doi.org/10.1021/jo701694k.

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42

Si, Anshupriya, and Steven J. Sucheck. "Synthesis of Aminooxy Glycoside Derivatives of the Outer Core Domain of Pseudomonas aeruginosa Lipopolysaccharide." Frontiers in Molecular Biosciences 8 (November 8, 2021). http://dx.doi.org/10.3389/fmolb.2021.750502.

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Pseudomonas aeruginosa is a highly prevalent gram-negative bacterium that is becoming more difficult to treat because of increasing antibiotic resistance. As chemotherapeutic treatment options diminish, there is an increased need for vaccines. However, the creation of an effective P. aeruginosa vaccine has been elusive despite intensive efforts. Thus, new paradigms for vaccine antigens should be explored to develop effective vaccines. In these studies, we have focused on the synthesis of two L-rhamnose–bearing epitopes common to glycoforms I and II of the outer core domain of Pseudomonas aeruginosa lipopolysaccharide, α-L-Rha-(1→6)-α-D-Glc-(1→4)-α-D-GalN-(Ala)-α-aminooxy (3) and α-L-Rha-(1→3)-β-D-Glc-(1→3)-α-D-GalN-(Ala)-α-aminooxy (4), respectively. The target trisaccharides were both prepared starting from a suitably protected galactosamine glycoside, followed by successive deprotection and glycosylation with suitably protected D-glucose and L-rhamnose thioglycosides. Global deprotection resulted in the formation of targets 3 and 4 in 22 and 35% yield each. Care was required to modify basic reaction conditions to avoid early deprotection of the N-oxysuccinamido group. In summary, trisaccharides related to the L-rhamnose–bearing epitopes common to glycoforms I and II of the outer core domain of Pseudomonas aeruginosa lipopolysaccharide have been prepared as their aminooxy glycosides. The latter are expected to be useful in chemoselective oxime-based bioconjugation reactions to form Pseudomonas aeruginosa vaccines.

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43

Codee, Jeroen D. C., Leendert J. van den Bos, Remy E. J. N. Litjens, Herman S. Overkleeft, Constant A. A. van Boeckel, Jacques H. van Boom, and Gijs A. van der Marel. "Chemoselective Glycosylations Using Sulfonium Triflate Activator Systems." ChemInform 35, no. 24 (June 15, 2004). http://dx.doi.org/10.1002/chin.200424166.

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44

Codee, Jeroen D. C., Remy E. J. N. Litjens, Rene den Heeten, Herman S. Overkleeft, Jacques H. van Boom, and Gijs A. van der Marel. "Ph2SO/Tf2O: A Powerful Promotor System in Chemoselective Glycosylations Using Thioglycosides." ChemInform 34, no. 35 (September 2, 2003). http://dx.doi.org/10.1002/chin.200335160.

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45

Miermont, Adeline, Youlin Zeng, Yuqing Jing, Xin-shan Ye, and Xuefei Huang. "ChemInform Abstract: Syntheses of LewisXand Dimeric LewisX: Construction of Branched Oligosaccharides by a Combination of Preactivation and Reactivity Based Chemoselective One-Pot Glycosylations." ChemInform 39, no. 5 (January 29, 2008). http://dx.doi.org/10.1002/chin.200805195.

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