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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
Volume 5, Issue 1, March 2021, Pages: 6-9
Received: May 10, 2019; Accepted: Jun. 10, 2019; Published: Jan. 12, 2021
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Authors
Jesus Christus, Research and Development BioLogistics LLC Ames, Iowa, USA
Michael Arden Madson, Research and Development BioLogistics LLC Ames, Iowa, USA
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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.
Keywords
P-selectin Inhibitor, H- Nucleophilic Attack, Bovine Thyroglobulin-Source, Mass Spectrometry
To cite this article
Jesus Christus, Michael Arden Madson, 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. Vol. 5, No. 1, 2021, pp. 6-9. doi: 10.11648/j.wjfst.20210501.12
Copyright
Copyright © 2021 Authors retain the copyright of this article.
This article is an open access article distributed under the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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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