World Journal of Food Science and Technology

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Preparation of Possible P Selectin Inhibitor from Bovine Thyroglobulin, (Di-hydrido) Sulfo Hydrate 1, 5 Anhydro L-fucitol

Received: 10 May 2019    Accepted: 10 June 2019    Published: 12 January 2021
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Abstract

P selectin is known to mediate several disease states through the binding of epitopes on the surface of endothelial cells. These diseases include cancer, cancer metastasis and inflammation. Sulfo Lewis a is a sulfated oligosaccharide could bind P selectin. A possible novel inhibitor of P-selectin binding may attenuate these diseases. One possible inhibitor is prepared from bovine thyroglobulin in one step, with appropriate work-up, from a readily abundant source, bovine thyroid gland, via novel chemistry. That molecule is (di-hydrido) sulfo hydrate 1, 5 anhydro L-fucitol. This chemistry is known to occur for the preparation of 1, 5 anhydro oligosaccharides from K casein and bovine milk. Another example of this chemistry has also been prepared; the di-(hydrido) di-phosphate di-hydrate 2, 5 anhydro mannitol (glucitol) from an ethanol extract of banana fruit. The molecule, here, would be the first report of H- nucleophile attack of a non-phosphorylated glycoside. In addition to components of the O-linked oligosaccharide, to originate from bovine thyroglobulin requiring a tyrosine sulfate for binding. This work provides methods for preparing (di-hydrido) sulfo 1, 5 anhydro L-fucitol, as a possible inhibitor of P-selectin binding, in addition to those reported. These include; the di (di-hydrido) trisaccharide di-(hydrido) di-phosphate di-hydrate serinyl (di-hydrido) sulfo tyrosine dipeptide as well as the tri (di-hydrido) sulfo tri-hydrate 1, 5 anhydro trisaccharide alditol. Both of the latter two originate from bovine thyroglobulin and have been or will, possibly, be reported.

DOI 10.11648/j.wjfst.20210501.12
Published in World Journal of Food Science and Technology (Volume 5, Issue 1, March 2021)
Page(s) 6-9
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

P-selectin Inhibitor, H- Nucleophilic Attack, Bovine Thyroglobulin-Source, Mass Spectrometry

References
[1] Geng, J-G; Chen, M.; Chou, Kuo-C. P-selectin Cell Adhesion Molecule in Inflammation, Thrombosis, Cancer Growth and Metastasis Current Medicinal Chemistry 11 (16) 2153-2160 (8) (2004).
[2] Manning, D.; Hu, X.; Beck, P.; Kiessling, L.; Synthesis of Sulfated Neoglycopolymers: Selective P-Selectin Inhibitors Journal of the American Chemical Society 119 (13), 3161-3162 DOI: 10.1021/ja964046x (1997).
[3] Christus, J.’ Madson, M.; Possible treatment for malaria to mimic and inhibit Duffy Binding Protein II (DBP II) monomer 2 binding to DBP II monomer 1; sulfo tyrosine oligosaccharide dipeptide from bovine thyroglobulin World Journal of Food Science and Technology, manuscript under review (2019).
[4] Leppänen, A.; White, S.; Helin, J.; McEver, R.; Cummings, R.; Binding of Glycosulfopeptides to P-selectin Requires Stereospecific Contributions of Individual Tyrosine Sulfate and Sugar Residues J. Biol. Chem. 275 39569-39578 (2000).
[5] Christus, J.; Madson, M.; Preparation of 2, 5-anhydro di-(hydrido) di-phosphate di-hydrate Mannitol (Glucitol) from Banana Fruit Yields a Possible Fructose 1, 6 Bisphosphate Aldolase Inhibitor (s), accepted for publication, World Journal of Food Science and Technology (2019).
[6] Madson, M.; Affinity/lectin chromatography methods, patent, US 9, 522, 382 B2 (2016).
[7] Madson, M.; Method of discerning substitution of carbohydrate esters, patent, US 9, 726, 671 B2 (2017).
[8] Madson, M.; Manufacturing of MEOH, formaldehyde, formic acid and ammonium penta-borate tetra-hydrate from CO2, patent, US 8, 685, 355 B2 (2014).
[9] Christus, J.; Madson, M.; Possible Mimics of Duffy Binding Protein-II for Plasmodium vivax Binding Endothelial Cells or Binding Plasmodium falciparum by Mimicking Epitope on Erythrocyte Binding Antigen-175 A World Journal of Food Science and Technology 2 (2) 44-54 (2018).
[10] Christus, J.; Madson, M.; Possible Treatment of Mycobacterium lepramatous with Bovine Milk World Journal of Food Science and Technology 2 (3) 55-61 (2018).
[11] Norgard, K.; Moore, K.; Diaz, S.; Stults, N.; Ushiyama, S.; McEver, R.; Cummings, R.; Varki, A.; Characterization of a specific ligand for P-selectin on myeloid cells. A minor glycoprotein with sialylated O-linked oligosaccharides. J. of Biol. Chem. 268 12764-12774. (1993).
[12] Nelson, R.; Cecconi, O.; Roberts, W.; Aruffo, A.; Linhardt, R.; Bevilacqua, M.; Heparin oligosaccharides bind L- and P-selectin and inhibit acute inflammation Blood 82: 3253-3258; (1993).
[13] Malý, P.; Thall, A.; Petryniak, B.; Rogers, C.; Smith, P.; Marks, R.; Kelly, R.; 1 Gersten, K.; Cheng, G.; Saunders, T.; Camper, S.; Camphausen, R.,.; Sullivan, F.; YukihiroIsogai;, Hindsgaul, O.; Andrian, U.; Lowe, J.; The α (1, 3) Fucosyl transferase Fuc-TVII controls leukocyte trafficking through an essential role in L-, E-, and P-selectin ligand biosynthesis Cell 86 (4) 23 643-653 (1996).
[14] Ohmori, K.; Kanda, L.; Mitsuoka, C.; Kanamori, A.; Kurata-Miura, K.; Sasaki, K.; Nishi, T.; Tamatani, T.; Kannagi, R.; P- and E-Selectins recognize sialyl 6-sulfo lewis x, the recently Identified L-Selectin ligand Biochem. Biophys. Res. Commun. 278 (1) 90-96 (2000).
[15] Larsen, C.; Ridgway, B.; Shaw, J.; Woerpel, K.]; A Stereoelectronic Model To Explain the Highly Stereoselective Reactions of Nucleophiles with Five-Membered-Ring Oxocarbenium Ions Department of Chemistry, University of California Irvine, California 92697-2025 J. Am. Chem. Soc. 12 (151) 12208-12209 (1999).
Author Information
  • Research and Development BioLogistics LLC Ames, Iowa, USA

  • Research and Development BioLogistics LLC Ames, Iowa, USA

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    Jesus Christus, Michael Arden Madson. (2021). Preparation of Possible P Selectin Inhibitor from Bovine Thyroglobulin, (Di-hydrido) Sulfo Hydrate 1, 5 Anhydro L-fucitol. World Journal of Food Science and Technology, 5(1), 6-9. https://doi.org/10.11648/j.wjfst.20210501.12

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    ACS Style

    Jesus Christus; Michael Arden Madson. Preparation of Possible P Selectin Inhibitor from Bovine Thyroglobulin, (Di-hydrido) Sulfo Hydrate 1, 5 Anhydro L-fucitol. World J. Food Sci. Technol. 2021, 5(1), 6-9. doi: 10.11648/j.wjfst.20210501.12

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    AMA Style

    Jesus Christus, Michael Arden Madson. Preparation of Possible P Selectin Inhibitor from Bovine Thyroglobulin, (Di-hydrido) Sulfo Hydrate 1, 5 Anhydro L-fucitol. World J Food Sci Technol. 2021;5(1):6-9. doi: 10.11648/j.wjfst.20210501.12

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  • @article{10.11648/j.wjfst.20210501.12,
      author = {Jesus Christus and Michael Arden Madson},
      title = {Preparation of Possible P Selectin Inhibitor from Bovine Thyroglobulin, (Di-hydrido) Sulfo Hydrate 1, 5 Anhydro L-fucitol},
      journal = {World Journal of Food Science and Technology},
      volume = {5},
      number = {1},
      pages = {6-9},
      doi = {10.11648/j.wjfst.20210501.12},
      url = {https://doi.org/10.11648/j.wjfst.20210501.12},
      eprint = {https://download.sciencepg.com/pdf/10.11648.j.wjfst.20210501.12},
      abstract = {P selectin is known to mediate several disease states through the binding of epitopes on the surface of endothelial cells. These diseases include cancer, cancer metastasis and inflammation. Sulfo Lewis a is a sulfated oligosaccharide could bind P selectin. A possible novel inhibitor of P-selectin binding may attenuate these diseases. One possible inhibitor is prepared from bovine thyroglobulin in one step, with appropriate work-up, from a readily abundant source, bovine thyroid gland, via novel chemistry. That molecule is (di-hydrido) sulfo hydrate 1, 5 anhydro L-fucitol. This chemistry is known to occur for the preparation of 1, 5 anhydro oligosaccharides from K casein and bovine milk. Another example of this chemistry has also been prepared; the di-(hydrido) di-phosphate di-hydrate 2, 5 anhydro mannitol (glucitol) from an ethanol extract of banana fruit. The molecule, here, would be the first report of H- nucleophile attack of a non-phosphorylated glycoside. In addition to components of the O-linked oligosaccharide, to originate from bovine thyroglobulin requiring a tyrosine sulfate for binding. This work provides methods for preparing (di-hydrido) sulfo 1, 5 anhydro L-fucitol, as a possible inhibitor of P-selectin binding, in addition to those reported. These include; the di (di-hydrido) trisaccharide di-(hydrido) di-phosphate di-hydrate serinyl (di-hydrido) sulfo tyrosine dipeptide as well as the tri (di-hydrido) sulfo tri-hydrate 1, 5 anhydro trisaccharide alditol. Both of the latter two originate from bovine thyroglobulin and have been or will, possibly, be reported.},
     year = {2021}
    }
    

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  • TY  - JOUR
    T1  - Preparation of Possible P Selectin Inhibitor from Bovine Thyroglobulin, (Di-hydrido) Sulfo Hydrate 1, 5 Anhydro L-fucitol
    AU  - Jesus Christus
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    DO  - 10.11648/j.wjfst.20210501.12
    T2  - World Journal of Food Science and Technology
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    JO  - World Journal of Food Science and Technology
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    PB  - Science Publishing Group
    SN  - 2637-6024
    UR  - https://doi.org/10.11648/j.wjfst.20210501.12
    AB  - P selectin is known to mediate several disease states through the binding of epitopes on the surface of endothelial cells. These diseases include cancer, cancer metastasis and inflammation. Sulfo Lewis a is a sulfated oligosaccharide could bind P selectin. A possible novel inhibitor of P-selectin binding may attenuate these diseases. One possible inhibitor is prepared from bovine thyroglobulin in one step, with appropriate work-up, from a readily abundant source, bovine thyroid gland, via novel chemistry. That molecule is (di-hydrido) sulfo hydrate 1, 5 anhydro L-fucitol. This chemistry is known to occur for the preparation of 1, 5 anhydro oligosaccharides from K casein and bovine milk. Another example of this chemistry has also been prepared; the di-(hydrido) di-phosphate di-hydrate 2, 5 anhydro mannitol (glucitol) from an ethanol extract of banana fruit. The molecule, here, would be the first report of H- nucleophile attack of a non-phosphorylated glycoside. In addition to components of the O-linked oligosaccharide, to originate from bovine thyroglobulin requiring a tyrosine sulfate for binding. This work provides methods for preparing (di-hydrido) sulfo 1, 5 anhydro L-fucitol, as a possible inhibitor of P-selectin binding, in addition to those reported. These include; the di (di-hydrido) trisaccharide di-(hydrido) di-phosphate di-hydrate serinyl (di-hydrido) sulfo tyrosine dipeptide as well as the tri (di-hydrido) sulfo tri-hydrate 1, 5 anhydro trisaccharide alditol. Both of the latter two originate from bovine thyroglobulin and have been or will, possibly, be reported.
    VL  - 5
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