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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.

Published in World Journal of Food Science and Technology (Volume 5, Issue 1)
DOI 10.11648/j.wjfst.20210501.12
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), 2021. 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).
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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://article.sciencepublishinggroup.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
    AU  - Michael Arden Madson
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    PY  - 2021
    N1  - https://doi.org/10.11648/j.wjfst.20210501.12
    DO  - 10.11648/j.wjfst.20210501.12
    T2  - World Journal of Food Science and Technology
    JF  - World Journal of Food Science and Technology
    JO  - World Journal of Food Science and Technology
    SP  - 6
    EP  - 9
    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
    IS  - 1
    ER  - 

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Author Information
  • Research and Development BioLogistics LLC Ames, Iowa, USA

  • Research and Development BioLogistics LLC Ames, Iowa, USA

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