Chemical synthesis using enzymatically generated building units for construction of the human milk pentasaccharides sialyllacto-N-tetraose and sialyllacto-N-neotetraose epimer

Dirk Schmidt and Joachim Thiem
Beilstein J. Org. Chem. 2010, 6, No. 18. https://doi.org/10.3762/bjoc.6.18

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Chemical synthesis using enzymatically generated building units for construction of the human milk pentasaccharides sialyllacto-N-tetraose and sialyllacto-N-neotetraose epimer
Dirk Schmidt and Joachim Thiem
Beilstein J. Org. Chem. 2010, 6, No. 18. https://doi.org/10.3762/bjoc.6.18

How to Cite

Schmidt, D.; Thiem, J. Beilstein J. Org. Chem. 2010, 6, No. 18. doi:10.3762/bjoc.6.18

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Scholarly Works

  • Guzmán-Rodríguez, F.; Alatorre-Santamaría, S.; Cruz-Guerrero, A. Human Milk Oligosaccharides (HMOS). Handbook of Food Bioactive Ingredients; Springer International Publishing, 2023; pp 1383–1411. doi:10.1007/978-3-031-28109-9_35
  • Guzmán-Rodríguez, F.; Alatorre-Santamaría, S.; Cruz-Guerrero, A. Human Milk Oligosaccharides (HMOS). Handbook of Food Bioactive Ingredients; Springer International Publishing, 2022; pp 1–29. doi:10.1007/978-3-030-81404-5_35-1
  • Lu, M.; Mosleh, I.; Abbaspourrad, A. Engineered Microbial Routes for Human Milk Oligosaccharides Synthesis. ACS synthetic biology 2021, 10, 923–938. doi:10.1021/acssynbio.1c00063
  • Zhu, Y.; Wan, L.; Li, W.; Ni, D.; Zhang, W.; Yan, X.; Mu, W. Recent advances on 2′-fucosyllactose: physiological properties, applications, and production approaches. Critical reviews in food science and nutrition 2020, 62, 1–10. doi:10.1080/10408398.2020.1850413
  • Marchesi, A.; Parmeggiani, F.; Louçano, J.; Mattey, A. P.; Huang, K.; Gupta, T.; Salwiczek, M.; Flitsch, S. L. Enzymatic Building Block Synthesis for Automated Solid Phase Glycan Assembly. Angewandte Chemie 2020, 132, 22642–22645. doi:10.1002/ange.202008067
  • Marchesi, A.; Parmeggiani, F.; Louçano, J.; Mattey, A. P.; Huang, K.; Gupta, T.; Salwiczek, M.; Flitsch, S. L. Enzymatic Building-Block Synthesis for Solid-Phase Automated Glycan Assembly. Angewandte Chemie (International ed. in English) 2020, 59, 22456–22459. doi:10.1002/anie.202008067
  • Pérez-Escalante, E.; Alatorre-Santamaría, S.; Castañeda-Ovando, A.; Salazar-Pereda, V.; Bautista-Ávila, M.; Cruz-Guerrero, A.; Flores-Aguilar, J. F.; González-Olivares, L. G. Human milk oligosaccharides as bioactive compounds in infant formula: recent advances and trends in synthetic methods. Critical reviews in food science and nutrition 2020, 62, 1–34. doi:10.1080/10408398.2020.1813683
  • Czaschke, C.; de Abreu, R. F.; Stark, C. B. W.; Thiem, J. Synthesis of Dideoxy-octonic Acid and Cyclic and Acyclic Derivatives Thereof. Organic letters 2020, 22, 3373–3376. doi:10.1021/acs.orglett.0c00842
  • Zeuner, B.; Teze, D.; Muschiol, J.; Meyer, A. S. Synthesis of Human Milk Oligosaccharides: Protein Engineering Strategies for Improved Enzymatic Transglycosylation. Molecules (Basel, Switzerland) 2019, 24, 2033. doi:10.3390/molecules24112033
  • Faijes, M.; Castejón-Vilatersana, M.; Val-Cid, C.; Planas, A. Enzymatic and cell factory approaches to the production of human milk oligosaccharides. Biotechnology advances 2019, 37, 667–697. doi:10.1016/j.biotechadv.2019.03.014
  • Sprenger, G. A.; Baumgärtner, F.; Albermann, C. Production of human milk oligosaccharides by enzymatic and whole-cell microbial biotransformations. Journal of biotechnology 2017, 258, 79–91. doi:10.1016/j.jbiotec.2017.07.030
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  • Chen, X. Human Milk Oligosaccharides (HMOS): Structure, Function, and Enzyme-Catalyzed Synthesis. Advances in carbohydrate chemistry and biochemistry 2015, 72, 113–190. doi:10.1016/bs.accb.2015.08.002
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  • Lütteke, T. The use of glycoinformatics in glycochemistry. Beilstein journal of organic chemistry 2012, 8, 915–929. doi:10.3762/bjoc.8.104
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Patents

  • JENNEWEIN STEFAN; WARTENBERG DIRK. SIALYLTRANSFERASES AND THEIR USE IN PRODUCING SIALYLATED OLIGOSACCHARIDES. WO 2019020707 A1, Jan 31, 2019.
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