Chemo-enzymatic modification of poly-N-acetyllactosamine (LacNAc) oligomers and N,N-diacetyllactosamine (LacDiNAc) based on galactose oxidase treatment

Christiane E. Kupper, Ruben R. Rosencrantz, Birgit Henßen, Helena Pelantová, Stephan Thönes, Anna Drozdová, Vladimir Křen and Lothar Elling
Beilstein J. Org. Chem. 2012, 8, 712–725. https://doi.org/10.3762/bjoc.8.80

Supporting Information

Supporting Information File 1: Additional diagrams, HPLC chromatograms and ESI–MS spectra.
Format: PDF Size: 829.5 KB Download
Supporting Information File 2: NMR data and spectra.
Format: PDF Size: 806.5 KB Download

Cite the Following Article

Chemo-enzymatic modification of poly-N-acetyllactosamine (LacNAc) oligomers and N,N-diacetyllactosamine (LacDiNAc) based on galactose oxidase treatment
Christiane E. Kupper, Ruben R. Rosencrantz, Birgit Henßen, Helena Pelantová, Stephan Thönes, Anna Drozdová, Vladimir Křen and Lothar Elling
Beilstein J. Org. Chem. 2012, 8, 712–725. https://doi.org/10.3762/bjoc.8.80

How to Cite

Kupper, C. E.; Rosencrantz, R. R.; Henßen, B.; Pelantová, H.; Thönes, S.; Drozdová, A.; Křen, V.; Elling, L. Beilstein J. Org. Chem. 2012, 8, 712–725. doi:10.3762/bjoc.8.80

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Wu, Y.; Bosman, G. P.; Vos, G. M.; Uslu, E.; Chapla, D.; Huang, C.; Moremen, K. W.; Boons, G.-J. Chemoenzymatic Synthesis of Keratan Sulfate Oligosaccharides Using UDP-Galactose-6-aldehyde To Control Sulfation at Galactosides. Organic letters 2024, 26, 8272–8277. doi:10.1021/acs.orglett.4c02899
  • Lu, N.; Li, Y.; Xia, H.; Zhong, K.; Jia, C.; Ye, J.; Liu, X.; Liu, C.-C.; Cao, H. A Redox-Controlled Substrate Engineering Strategy for Site-Specific Enzymatic Fucosylation. Angewandte Chemie (International ed. in English) 2022, 61, e202211032. doi:10.1002/anie.202211032
  • Lu, N.; Li, Y.; Xia, H.; Zhong, K.; Jia, C.; Ye, J.; Liu, X.; Liu, C.; Cao, H. A Redox‐Controlled Substrate Engineering Strategy for Site‐Specific Enzymatic Fucosylation. Angewandte Chemie 2022, 134. doi:10.1002/ange.202211032
  • Chen, C.-Y.; Lin, Y.-W.; Wang, S.-W.; Lin, Y.-C.; Cheng, Y.-Y.; Ren, C.-T.; Wong, C.-H.; Wu, C.-Y. Synthesis of Azido-Globo H Analogs for Immunogenicity Evaluation. ACS central science 2021, 8, 77–85. doi:10.1021/acscentsci.1c01277
  • Ziganshina, M. M.; Dolgushina, N. V.; Kulikova, G. V.; Fayzullina, N. M.; Yarotskaya, E.; Khasbiullina, N. R.; Abdurakhmanova, N. F.; Asaturova, A. V.; Shchegolev, A. I.; Dovgan, A. A.; Sukhikh, G. T. Epithelial apical glycosylation changes associated with thin endometrium in women with infertility - a pilot observational study. Reproductive biology and endocrinology : RB&E 2021, 19, 73. doi:10.1186/s12958-021-00750-z
  • Dussouy, C.; Téletchéa, S.; Lambert, A.; Charlier, C.; Botez, I.; De Ceuninck, F.; Grandjean, C. Access to Galectin-3 Inhibitors from Chemoenzymatic Synthons. The Journal of organic chemistry 2020, 85, 16099–16114. doi:10.1021/acs.joc.0c01927
  • Wang, Q.; Wang, T.; Yang, S.; Sha, S.; Wu, W. W.; Chen, Y.; Paul, J. T.; Shen, R.-F.; Cipollo, J. F.; Betenbaugh, M. J. Metabolic engineering challenges of extending N-glycan pathways in Chinese hamster ovary cells. Metabolic engineering 2020, 61, 301–314. doi:10.1016/j.ymben.2020.06.007
  • Storozhylova, N.; Crecente-Campo, J.; Cabaleiro, D.; Lugo, L.; Dussouy, C.; Simões, S.; Monteiro, M.; Grandjean, C.; Alonso, M. J. An In Situ Hyaluronic Acid-Fibrin Hydrogel Containing Drug-Loaded Nanocapsules for Intra-Articular Treatment of Inflammatory Joint Diseases. Regenerative Engineering and Translational Medicine 2020, 6, 201–216. doi:10.1007/s40883-020-00154-2
  • Cosgrove, S. C.; Mattey, A. P.; Riese, M.; Chapman, M. R.; Birmingham, W. R.; Blacker, A. J.; Kapur, N.; Turner, N. J.; Flitsch, S. L. Biocatalytic Oxidation in Continuous Flow for the Generation of Carbohydrate Dialdehydes. ACS Catalysis 2019, 9, 11658–11662. doi:10.1021/acscatal.9b04819
  • Lu, N.; Ye, J.; Cheng, J.; Sasmal, A.; Liu, C.-C.; Yao, W.; Yan, J.; Khan, N.; Yi, W.; Varki, A.; Cao, H. Redox-Controlled Site-Specific α2–6-Sialylation. Journal of the American Chemical Society 2019, 141, 4547–4552. doi:10.1021/jacs.9b00044
  • Laaf, D.; Bojarová, P.; Elling, L.; Křen, V. Galectin-Carbohydrate Interactions in Biomedicine and Biotechnology. Trends in biotechnology 2018, 37, 402–415. doi:10.1016/j.tibtech.2018.10.001
  • Bumba, L.; Laaf, D.; Spiwok, V.; Elling, L.; Křen, V.; Bojarová, P. Poly-N-Acetyllactosamine Neo-Glycoproteins as Nanomolar Ligands of Human Galectin-3: Binding Kinetics and Modeling. International journal of molecular sciences 2018, 19, 372. doi:10.3390/ijms19020372
  • Huang, K.; Parmeggiani, F.; Pallister, E.; Huang, C.-J.; Liu, F.-F.; Li, Q.; Birmingham, W. R.; Both, P.; Thomas, B.; Liu, L.; Voglmeir, J.; Flitsch, S. L. Characterisation of a Bacterial Galactokinase with High Activity and Broad Substrate Tolerance for Chemoenzymatic Synthesis of 6-Aminogalactose-1-Phosphate and Analogues. Chembiochem : a European journal of chemical biology 2018, 19, 388–394. doi:10.1002/cbic.201700477
  • Laaf, D.; Steffens, H.; Pelantová, H.; Bojarová, P.; Křen, V.; Elling, L. Chemo-Enzymatic Synthesis of Branched N -Acetyllactosamine Glycan Oligomers for Galectin-3 Inhibition. Advanced Synthesis & Catalysis 2017, 359, 4015–4024. doi:10.1002/adsc.201700969
  • Laaf, D.; Bojarová, P.; Pelantová, H.; Křen, V.; Elling, L. Tailored Multivalent Neo-Glycoproteins: Synthesis, Evaluation, and Application of a Library of Galectin-3-Binding Glycan Ligands. Bioconjugate chemistry 2017, 28, 2832–2840. doi:10.1021/acs.bioconjchem.7b00520
  • Böcker, S.; Elling, L. Biotinylated N-Acetyllactosamine- and N,N-Diacetyllactosamine-Based Oligosaccharides as Novel Ligands for Human Galectin-3. Bioengineering (Basel, Switzerland) 2017, 4, 31. doi:10.3390/bioengineering4020031
  • Wahl, C.; Hirtz, D.; Elling, L. Multiplexed capillary electrophoresis as analytical tool for fast optimization of multi-enzyme cascade reactions synthesis of nucleotide sugars. Biotechnology journal 2016, 11, 1298–1308. doi:10.1002/biot.201600265
  • Rosencrantz, R. R.; Nguyen, V. H.; Park, H.; Schulte, C.; Böker, A.; Schnakenberg, U.; Elling, L. Lectin binding studies on a glycopolymer brush flow-through biosensor by localized surface plasmon resonance. Analytical and bioanalytical chemistry 2016, 408, 5633–5640. doi:10.1007/s00216-016-9667-9
  • Lange, B.; Simonova, A.; Fischöder, T.; Pelantová, H.; Křen, V.; Elling, L. Towards Keratan Sulfate – Chemoenzymatic Cascade Synthesis of Sulfated N‐Acetyllactosamine (LacNAc) Glycan Oligomers. Advanced Synthesis & Catalysis 2016, 358, 584–596. doi:10.1002/adsc.201500916
  • Parikka, K.; Master, E. R.; Tenkanen, M. Oxidation with galactose oxidase: Multifunctional enzymatic catalysis. Journal of Molecular Catalysis B: Enzymatic 2015, 120, 47–59. doi:10.1016/j.molcatb.2015.06.006

Patents

  • PITCOVSKI JACOB; VAYA JACOB; KHATIB SOLIMAN; AIZENSHTEIN ELINA; GEFEN TAL. Proteins modified with (amino) monosaccharide-biotin adduct. US 10821179 B2, Nov 3, 2020.
  • PITCOVSKI JACOB; VAYA JACOB; KHATIB SOLIMAN; AIZENSHTEIN ALINA; GEFEN TAL. PROTEINS MODIFIED WITH (AMINO) MONOSACCHARIDE-BIOTIN ADDUCT. US 20120156227 A1, June 21, 2012.
Other Beilstein-Institut Open Science Activities