Science Journal of Chemistry

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Osidic Bridges of Amylose and Amylopectin Degradations by Water Molecules: Formulation of a Mechanism

Received: 27 September 2023    Accepted: 26 October 2023    Published: 9 November 2023
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Abstract

Rapid rot of plantain causes post-harvest loss of at least 30%. It can be a source of food insecurity for consuming populations. It is linked to its polysaccharide degradation. Proposed physicochemical solutions have still not made it possible to significantly reduce this risk. Its main origin isn’t considered. This compound is formed of amylose and amylopectin. Our previous works attempted to understand this process as a first step. This knowledge may facilitate the solutions to protect these polysaccharides. The mechanism of their degradation under the action of a single water molecule is simulated. Amylose with four (AM4G) or five (AM5G) building blocks is broken down into disaccharides; amylopectin with four synthons (AMP4G) into trisaccharides and with five (AMP5G) is transformed into tetra-saccharides. The destructive hydrogen bonds (HB) are located around the osidic bridge targeted by the H2O. Higher-order oxygen seems to participate. However, this work allowed us to partially understand this mechanism. The links underlying starch splitting are not shown. The modalities of its deterioration following the simultaneous attack of two H2O are unknown. This article aims to address these weaknesses. This research directs to establish the mechanism of starch degradation under the combined action of two H2O. It intends to explain the connections involved in these processes. To do this, its method relies on the resources of quantum chemistry. Interactions polysaccharide-water is assessed by ONIOM method [ONIOM (B3LYP/6-311++G(d, p): AM1)]. Their energies and the electronic charge transfer are provided by the Natural Bond Orbital calculations. The geometric, energetic, spectroscopic parameters of the molecules and the electron density are generated with Gaussian09. The preferred HB sites for AM4G or AMP4G are respectively O37 (O2sp3) and O63 (O'3sp3). Oxygen O37 (O2sp3) is an HB anchor for AM5G. O14 (O'1sp3) and O86 (O'4sp3) are for those of AMP5G. In addition, amylose is degraded before the latter. The division of the complexes into several bonds results from the interactions of the H2O on the different saccharide bridges of the synthons. Thus, the O14-C25, O37-C46 and O58-C67 are involved in the cleavage of AM4G. The O13-C21, O55-C65 and O63-C43 are in that of AMP4G. The O14-C25, O37-C46 and C50-O58 and O79-C107 are associated with that of AM5G. O14-C25, O35-C44, O78-C88 and C30-O86 are those connected to AMP5G.

DOI 10.11648/j.sjc.20231106.11
Published in Science Journal of Chemistry (Volume 11, Issue 6, December 2023)
Page(s) 197-211
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

Starch, ONIOM, NBO Analysis, Hydrogen Bonds, Amylose and Amylopectin

References
[1] Yao K. Augustin, Koffi Djary M., Zaouli B. Irié and Niamké L. Sébastien. 2004. Effet de la substitution partielle de la farine de blé par la purée de la banane plantain (Musa AAB) bien mûre sur la qualité des produits de pâtisserie. J. Applied Biosci, 82, 7436–7448. https://doi.org/10.4314/jab.v82i1.12
[2] Cordenunsi B. R. and Lajolo FM. 1995. Starch breakdown during banana ripening: sucrose synthase and sucrose phosphate synthase. J. Agric. Food Chem., 43, 363–372. https://doi.org/10.1021/jf00050a016
[3] Lepengue Alexis N., Mouaragadja Isaac, Dick Emmanuel, Mbatchi Bertrand and Aké Sévérin. 2010. Amélioration de la durée de conservation des bananes plantain aux températures ambiantes, Int. J. Biol. Chem. Sci. 4(3), 730–737.
[4] Able Anoh Valentin, N’Guessan Boka Robert and Bamba El-Hadji Sawaliho. 2020. Monosaccharide Degradation Analysis by Functional Density Theory at Level B3lyp/6-311G (d, p). Op. Acc. J. Bio. Sci and Res, 6(2). DOI: 10.46718/JBGSR.2020.06.000144.
[5] Momany F. A, Appell M., Starti G., and Willett J. L. 2004. B3LYP/6-311++G** study of monohydrates of α- and β-D-glucopyranose: hydrogen bonding, stress energies, and effect of hydration on internal coordinates. Carbohydr. Res., 338, 553–567. https://doi.org/10.1016/j.carres.2003.10.013.
[6] Able Anoh Valentin, N’Guessan Boka Robert and Bamba El-Hadji Sawaliho. 2021. Hydrogen Bonds Sites of Amylose or Amylopectin from Starch at the ONIOM Level (B3LYP/6-311++G [d, p]: AM1). Computational Chemistry, 9, 85–96. DOI: 10.4236/cc.2021.91005.
[7] Lachi Nadia. 2015. Étude des Complexes d’inclusion par la méthode ONION. Guelma (Algérie): Université, 8 mai 1945, Faculté des mathématiques et de l’informatique et des sciences de la matière.
[8] Theivarasu C. and Murugesan R., 2016. «Natural bond orbital (NBO) population analysis of an energetic molecule 1-phenyl-2-nitroguanidine,» Int. J. Chem. Sci., 14 (14), 2019-2050.
[9] Michael J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb and D. J. Fox. 2009, Gaussian09, Revision D. 01. Gaussian Inc., Wallingford, CT.
[10] Jeffrey G. A. and Seanger W. 1991. Hydrogen Bonding in Biological Structures, Springer Berlin. https://doi.org/10.1007/978-3-642-85135-3
[11] Rowland R. S. and Taylor R. 1996. Intermolecular nonbonded contact distances in organic crystal structures: Comparison with distances expected from Van der Waals radii, J. Phys. Chem. 100, 7384–7391. https://doi.org/10.1021/jp953141+
[12] Jorly J. and Eluvathingal D. J. 2007. Red-, Blue-, or No-Shift in Hydrogen Bonds: A Unified Explanation. Journal of the American Chemical Society, 129, 4620–4632. https://doi.org/10.1021/ja067545z
[13] Bondi A. 1964. Van der Waals volumes and radii J. Phys. Chem., 68, 441–451. https://doi.org/10.1021/j100785a001
[14] Desiraju G. R. and Steiner T., 1999. The Weak Hydrogen Bond: In Struct. Chem. and Biol. (Oxford University Press.)
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    Robert, N. B., Valentin, A. A., Sawaliho, B. E. H. (2023). Osidic Bridges of Amylose and Amylopectin Degradations by Water Molecules: Formulation of a Mechanism. Science Journal of Chemistry, 11(6), 197-211. https://doi.org/10.11648/j.sjc.20231106.11

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    ACS Style

    Robert, N. B.; Valentin, A. A.; Sawaliho, B. E. H. Osidic Bridges of Amylose and Amylopectin Degradations by Water Molecules: Formulation of a Mechanism. Sci. J. Chem. 2023, 11(6), 197-211. doi: 10.11648/j.sjc.20231106.11

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    AMA Style

    Robert NB, Valentin AA, Sawaliho BEH. Osidic Bridges of Amylose and Amylopectin Degradations by Water Molecules: Formulation of a Mechanism. Sci J Chem. 2023;11(6):197-211. doi: 10.11648/j.sjc.20231106.11

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  • @article{10.11648/j.sjc.20231106.11,
      author = {N’Guessan Boka Robert and Ablé Anoh Valentin and Bamba El Hadji Sawaliho},
      title = {Osidic Bridges of Amylose and Amylopectin Degradations by Water Molecules: Formulation of a Mechanism},
      journal = {Science Journal of Chemistry},
      volume = {11},
      number = {6},
      pages = {197-211},
      doi = {10.11648/j.sjc.20231106.11},
      url = {https://doi.org/10.11648/j.sjc.20231106.11},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20231106.11},
      abstract = {Rapid rot of plantain causes post-harvest loss of at least 30%. It can be a source of food insecurity for consuming populations. It is linked to its polysaccharide degradation. Proposed physicochemical solutions have still not made it possible to significantly reduce this risk. Its main origin isn’t considered. This compound is formed of amylose and amylopectin. Our previous works attempted to understand this process as a first step. This knowledge may facilitate the solutions to protect these polysaccharides. The mechanism of their degradation under the action of a single water molecule is simulated. Amylose with four (AM4G) or five (AM5G) building blocks is broken down into disaccharides; amylopectin with four synthons (AMP4G) into trisaccharides and with five (AMP5G) is transformed into tetra-saccharides. The destructive hydrogen bonds (HB) are located around the osidic bridge targeted by the H2O. Higher-order oxygen seems to participate. However, this work allowed us to partially understand this mechanism. The links underlying starch splitting are not shown. The modalities of its deterioration following the simultaneous attack of two H2O are unknown. This article aims to address these weaknesses. This research directs to establish the mechanism of starch degradation under the combined action of two H2O. It intends to explain the connections involved in these processes. To do this, its method relies on the resources of quantum chemistry. Interactions polysaccharide-water is assessed by ONIOM method [ONIOM (B3LYP/6-311++G(d, p): AM1)]. Their energies and the electronic charge transfer are provided by the Natural Bond Orbital calculations. The geometric, energetic, spectroscopic parameters of the molecules and the electron density are generated with Gaussian09. The preferred HB sites for AM4G or AMP4G are respectively O37 (O2sp3) and O63 (O'3sp3). Oxygen O37 (O2sp3) is an HB anchor for AM5G. O14 (O'1sp3) and O86 (O'4sp3) are for those of AMP5G. In addition, amylose is degraded before the latter. The division of the complexes into several bonds results from the interactions of the H2O on the different saccharide bridges of the synthons. Thus, the O14-C25, O37-C46 and O58-C67 are involved in the cleavage of AM4G. The O13-C21, O55-C65 and O63-C43 are in that of AMP4G. The O14-C25, O37-C46 and C50-O58 and O79-C107 are associated with that of AM5G. O14-C25, O35-C44, O78-C88 and C30-O86 are those connected to AMP5G.
    },
     year = {2023}
    }
    

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  • TY  - JOUR
    T1  - Osidic Bridges of Amylose and Amylopectin Degradations by Water Molecules: Formulation of a Mechanism
    AU  - N’Guessan Boka Robert
    AU  - Ablé Anoh Valentin
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    DO  - 10.11648/j.sjc.20231106.11
    T2  - Science Journal of Chemistry
    JF  - Science Journal of Chemistry
    JO  - Science Journal of Chemistry
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    EP  - 211
    PB  - Science Publishing Group
    SN  - 2330-099X
    UR  - https://doi.org/10.11648/j.sjc.20231106.11
    AB  - Rapid rot of plantain causes post-harvest loss of at least 30%. It can be a source of food insecurity for consuming populations. It is linked to its polysaccharide degradation. Proposed physicochemical solutions have still not made it possible to significantly reduce this risk. Its main origin isn’t considered. This compound is formed of amylose and amylopectin. Our previous works attempted to understand this process as a first step. This knowledge may facilitate the solutions to protect these polysaccharides. The mechanism of their degradation under the action of a single water molecule is simulated. Amylose with four (AM4G) or five (AM5G) building blocks is broken down into disaccharides; amylopectin with four synthons (AMP4G) into trisaccharides and with five (AMP5G) is transformed into tetra-saccharides. The destructive hydrogen bonds (HB) are located around the osidic bridge targeted by the H2O. Higher-order oxygen seems to participate. However, this work allowed us to partially understand this mechanism. The links underlying starch splitting are not shown. The modalities of its deterioration following the simultaneous attack of two H2O are unknown. This article aims to address these weaknesses. This research directs to establish the mechanism of starch degradation under the combined action of two H2O. It intends to explain the connections involved in these processes. To do this, its method relies on the resources of quantum chemistry. Interactions polysaccharide-water is assessed by ONIOM method [ONIOM (B3LYP/6-311++G(d, p): AM1)]. Their energies and the electronic charge transfer are provided by the Natural Bond Orbital calculations. The geometric, energetic, spectroscopic parameters of the molecules and the electron density are generated with Gaussian09. The preferred HB sites for AM4G or AMP4G are respectively O37 (O2sp3) and O63 (O'3sp3). Oxygen O37 (O2sp3) is an HB anchor for AM5G. O14 (O'1sp3) and O86 (O'4sp3) are for those of AMP5G. In addition, amylose is degraded before the latter. The division of the complexes into several bonds results from the interactions of the H2O on the different saccharide bridges of the synthons. Thus, the O14-C25, O37-C46 and O58-C67 are involved in the cleavage of AM4G. The O13-C21, O55-C65 and O63-C43 are in that of AMP4G. The O14-C25, O37-C46 and C50-O58 and O79-C107 are associated with that of AM5G. O14-C25, O35-C44, O78-C88 and C30-O86 are those connected to AMP5G.
    
    VL  - 11
    IS  - 6
    ER  - 

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Author Information
  • Laboratory of Constitution and Reaction of Matter, Unity of Formation and Research Science of Structure Matter and Technology, University Félix Houphouet-Boigny, Abidjan, Côte d’Ivoire

  • Laboratory of Constitution and Reaction of Matter, Unity of Formation and Research Science of Structure Matter and Technology, University Félix Houphouet-Boigny, Abidjan, Côte d’Ivoire

  • Laboratory of Constitution and Reaction of Matter, Unity of Formation and Research Science of Structure Matter and Technology, University Félix Houphouet-Boigny, Abidjan, Côte d’Ivoire

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