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)

Jesus’ Christus; Michael Arden Madson

doi:doi:10.11648/j.wjfst.20210501.11

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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)

Jesus’ Christus, Michael Arden Madson

Published in World Journal of Food Science and Technology (Volume 5, Issue 1)

Received: 26 January 2019 Accepted: 11 March 2019 Published: 12 January 2021

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Abstract

With previously unknown chemistry, 2,5-anhydro di-(hydrido)-di-phosphate-di-hydrate mannitol (glucitol) has (have) been prepared by H^- nucleophilic attack of neokestose-1,6-di-phosphate from commercial banana fruit. Negative ion mass spectrometry, Inductively Coupled Mass Spectrometry (ICP-MS), both ms and ms², has been used to characterize the product of this reaction. NaBH₄ in NH₄OH (pH 11.4, IN) for 18 hours was used to convert the 1,6-di-phospho neokestose to the 2,5 anhydro derivative(s). This molecule(s) are structural analogues of the known inhibitors of fructose-1,6 bisphosphate aldolase. The known inhibitors are 2,5 anhydro mannitol and 2,5 anhydro glucitol. They have K_is in the range of 10^-3 mM. It is expected that the di-(hydrido) di-phosphate di-hydrate 2,5 anhydro mannitol (glucitol), prepared here, may be tighter binding to fructose bisphosphate aldolase than the known non-phosphorylated inhibitors, because of their structural similarity to the substrate of the enzyme, fructose-1,6-bisphosphate. If the prepared molecule(s) bind to fbp aldolase, their preparation from inexpensive banana fruit would lead to an inexpensive method for treating fast growing cancer cells. The low cost of making the molecule(s) would allow access to cancer treatment by destitute or low income people.

Published in	World Journal of Food Science and Technology (Volume 5, Issue 1)
DOI	10.11648/j.wjfst.20210501.11
Page(s)	1-5
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

Banana Fruit, Fructose-1,6-bisphosphate Aldolase (Fbp Aldolase) Inhibitors, Synthesis, Mass Spectrometry

References

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[2]	Gray, G.; Barker, R.; Studies on the substrate of D-fructose 1,6 diphosphate aldolase in solution Biochemistry 9 (12) 2458-2462 (1970).
[3]	Heinrich, J.; Koenig, W.; Bretting, H.; Separations of permethylated monosaccharides and 1,5 anhydro alditols and simultaneous determination of linkage positions and absolute configuration in the galactan of Helix pomatia. Carbohydr. Res. 299 (1-2) 1-6 (1997).
[4]	Hartman, F.; Barker, R.; An exploration of the active site of aldolase using structural analogues of fructose diphosphate Biochemistry 4 (6) 1068-1075 (1965).
[5]	Madson, M.; Method of isolating and identifying fruit oligosaccharides from ripe banana fruit US 9557335 B2 (2017).
[6]	Madson, M; Mass Spectrometry Techniques for the structural characterization of glycans, Elsevier, New York, Amsterdam (2016).
[7]	Christus, J.; Madson, M.; Structural characterization of a compound from the ethanol extract of banana fruit poster Spring ACS National Meeting, Denver CO (2015).
[8]	Deslongchamps, P.; Stereoelectronic control in the cleavage of tetrahedral intermediates in the hydrolysis of esters and amides Tetrahedron 31 (20) 2463-2490 (1975).
[9]	Deslongchamps, P.; Rowan, D.; Pothier, N.; G.; Saunders, J.; 1, 7-Dioxaspiro [5.5] undecanes. An excellent system for the study of stereoelectronic effects (anomeric and exo-anomeric effects) in acetals Canadian Journal of Chemistry 59 (7) 1105-1121 (1981).
[10]	Christus, J.; Madson, M.; Possible treatment of Mycobacterium Lepromatous with bovine milk World Journal of Food Science and Technology 2 (3) 55-61 (2018).
[11]	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).
[12]	Rolf, D.; Gray, G.; Reductive cleavage of glycosides J. Am. Chem. Soc. 104 (12) 3539–354 (1982).
[13]	Rolf, D.; Gray, G.; Analysis of the linkage positions in D-fructofuranosyl residues by the reductive-cleavage method Carbohydr. Res. 131 (1) 17-28 (1984).

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APA Style

Jesus’ Christus, Michael Arden Madson. (2021). 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). World Journal of Food Science and Technology, 5(1), 1-5. https://doi.org/10.11648/j.wjfst.20210501.11

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ACS Style

Jesus’ Christus; Michael Arden Madson. 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). World J. Food Sci. Technol. 2021, 5(1), 1-5. doi: 10.11648/j.wjfst.20210501.11

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AMA Style

Jesus’ Christus, Michael Arden Madson. 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). World J Food Sci Technol. 2021;5(1):1-5. doi: 10.11648/j.wjfst.20210501.11

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@article{10.11648/j.wjfst.20210501.11,
  author = {Jesus’ Christus and Michael Arden Madson},
  title = {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)},
  journal = {World Journal of Food Science and Technology},
  volume = {5},
  number = {1},
  pages = {1-5},
  doi = {10.11648/j.wjfst.20210501.11},
  url = {https://doi.org/10.11648/j.wjfst.20210501.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.wjfst.20210501.11},
  abstract = {With previously unknown chemistry, 2,5-anhydro di-(hydrido)-di-phosphate-di-hydrate mannitol (glucitol) has (have) been prepared by H- nucleophilic attack of neokestose-1,6-di-phosphate from commercial banana fruit. Negative ion mass spectrometry, Inductively Coupled Mass Spectrometry (ICP-MS), both ms and ms2, has been used to characterize the product of this reaction. NaBH4 in NH4OH (pH 11.4, IN) for 18 hours was used to convert the 1,6-di-phospho neokestose to the 2,5 anhydro derivative(s). This molecule(s) are structural analogues of the known inhibitors of fructose-1,6 bisphosphate aldolase. The known inhibitors are 2,5 anhydro mannitol and 2,5 anhydro glucitol. They have Kis in the range of 10-3 mM. It is expected that the di-(hydrido) di-phosphate di-hydrate 2,5 anhydro mannitol (glucitol), prepared here, may be tighter binding to fructose bisphosphate aldolase than the known non-phosphorylated inhibitors, because of their structural similarity to the substrate of the enzyme, fructose-1,6-bisphosphate. If the prepared molecule(s) bind to fbp aldolase, their preparation from inexpensive banana fruit would lead to an inexpensive method for treating fast growing cancer cells. The low cost of making the molecule(s) would allow access to cancer treatment by destitute or low income people.},
 year = {2021}
}

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TY  - JOUR
T1  - 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)
AU  - Jesus’ Christus
AU  - Michael Arden Madson
Y1  - 2021/01/12
PY  - 2021
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DO  - 10.11648/j.wjfst.20210501.11
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  - 1
EP  - 5
PB  - Science Publishing Group
SN  - 2637-6024
UR  - https://doi.org/10.11648/j.wjfst.20210501.11
AB  - With previously unknown chemistry, 2,5-anhydro di-(hydrido)-di-phosphate-di-hydrate mannitol (glucitol) has (have) been prepared by H- nucleophilic attack of neokestose-1,6-di-phosphate from commercial banana fruit. Negative ion mass spectrometry, Inductively Coupled Mass Spectrometry (ICP-MS), both ms and ms2, has been used to characterize the product of this reaction. NaBH4 in NH4OH (pH 11.4, IN) for 18 hours was used to convert the 1,6-di-phospho neokestose to the 2,5 anhydro derivative(s). This molecule(s) are structural analogues of the known inhibitors of fructose-1,6 bisphosphate aldolase. The known inhibitors are 2,5 anhydro mannitol and 2,5 anhydro glucitol. They have Kis in the range of 10-3 mM. It is expected that the di-(hydrido) di-phosphate di-hydrate 2,5 anhydro mannitol (glucitol), prepared here, may be tighter binding to fructose bisphosphate aldolase than the known non-phosphorylated inhibitors, because of their structural similarity to the substrate of the enzyme, fructose-1,6-bisphosphate. If the prepared molecule(s) bind to fbp aldolase, their preparation from inexpensive banana fruit would lead to an inexpensive method for treating fast growing cancer cells. The low cost of making the molecule(s) would allow access to cancer treatment by destitute or low income people.
VL  - 5
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Author Information

Jesus’ Christus

Research & Development, Bio Logistics Limited Liability Corporation, Ames, Iowa, USA
Michael Arden Madson

Research & Development, Bio Logistics Limited Liability Corporation, Ames, Iowa, USA

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APA Style

Jesus’ Christus, Michael Arden Madson. (2021). 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). World Journal of Food Science and Technology, 5(1), 1-5. https://doi.org/10.11648/j.wjfst.20210501.11

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ACS Style

Jesus’ Christus; Michael Arden Madson. 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). World J. Food Sci. Technol. 2021, 5(1), 1-5. doi: 10.11648/j.wjfst.20210501.11

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AMA Style

Jesus’ Christus, Michael Arden Madson. 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). World J Food Sci Technol. 2021;5(1):1-5. doi: 10.11648/j.wjfst.20210501.11

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@article{10.11648/j.wjfst.20210501.11,
  author = {Jesus’ Christus and Michael Arden Madson},
  title = {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)},
  journal = {World Journal of Food Science and Technology},
  volume = {5},
  number = {1},
  pages = {1-5},
  doi = {10.11648/j.wjfst.20210501.11},
  url = {https://doi.org/10.11648/j.wjfst.20210501.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.wjfst.20210501.11},
  abstract = {With previously unknown chemistry, 2,5-anhydro di-(hydrido)-di-phosphate-di-hydrate mannitol (glucitol) has (have) been prepared by H- nucleophilic attack of neokestose-1,6-di-phosphate from commercial banana fruit. Negative ion mass spectrometry, Inductively Coupled Mass Spectrometry (ICP-MS), both ms and ms2, has been used to characterize the product of this reaction. NaBH4 in NH4OH (pH 11.4, IN) for 18 hours was used to convert the 1,6-di-phospho neokestose to the 2,5 anhydro derivative(s). This molecule(s) are structural analogues of the known inhibitors of fructose-1,6 bisphosphate aldolase. The known inhibitors are 2,5 anhydro mannitol and 2,5 anhydro glucitol. They have Kis in the range of 10-3 mM. It is expected that the di-(hydrido) di-phosphate di-hydrate 2,5 anhydro mannitol (glucitol), prepared here, may be tighter binding to fructose bisphosphate aldolase than the known non-phosphorylated inhibitors, because of their structural similarity to the substrate of the enzyme, fructose-1,6-bisphosphate. If the prepared molecule(s) bind to fbp aldolase, their preparation from inexpensive banana fruit would lead to an inexpensive method for treating fast growing cancer cells. The low cost of making the molecule(s) would allow access to cancer treatment by destitute or low income people.},
 year = {2021}
}

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TY  - JOUR
T1  - 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)
AU  - Jesus’ Christus
AU  - Michael Arden Madson
Y1  - 2021/01/12
PY  - 2021
N1  - https://doi.org/10.11648/j.wjfst.20210501.11
DO  - 10.11648/j.wjfst.20210501.11
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  - 1
EP  - 5
PB  - Science Publishing Group
SN  - 2637-6024
UR  - https://doi.org/10.11648/j.wjfst.20210501.11
AB  - With previously unknown chemistry, 2,5-anhydro di-(hydrido)-di-phosphate-di-hydrate mannitol (glucitol) has (have) been prepared by H- nucleophilic attack of neokestose-1,6-di-phosphate from commercial banana fruit. Negative ion mass spectrometry, Inductively Coupled Mass Spectrometry (ICP-MS), both ms and ms2, has been used to characterize the product of this reaction. NaBH4 in NH4OH (pH 11.4, IN) for 18 hours was used to convert the 1,6-di-phospho neokestose to the 2,5 anhydro derivative(s). This molecule(s) are structural analogues of the known inhibitors of fructose-1,6 bisphosphate aldolase. The known inhibitors are 2,5 anhydro mannitol and 2,5 anhydro glucitol. They have Kis in the range of 10-3 mM. It is expected that the di-(hydrido) di-phosphate di-hydrate 2,5 anhydro mannitol (glucitol), prepared here, may be tighter binding to fructose bisphosphate aldolase than the known non-phosphorylated inhibitors, because of their structural similarity to the substrate of the enzyme, fructose-1,6-bisphosphate. If the prepared molecule(s) bind to fbp aldolase, their preparation from inexpensive banana fruit would lead to an inexpensive method for treating fast growing cancer cells. The low cost of making the molecule(s) would allow access to cancer treatment by destitute or low income people.
VL  - 5
IS  - 1
ER  -

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